Preparation method of heterocyclic compound

Abstract

The invention relates to a preparation method of a compound as shown in a formula (I), which comprises the following steps: S1, carrying out reaction 1 on a compound a1 or a2 in the presence of Lewis acid and H2O2, and carrying out reaction 2 on the product in the presence of alkali to obtain a compound b; s2, the compound b is subjected to a reaction 3 in the presence of chloride and a catalyst, a product is subjected to a reaction 4, and the compound shown in the formula (I) is obtained. The method has the advantages of high reaction yield, high product purity, avoidance of generation of toxic substances, environmental friendliness, simplicity, high efficiency, mild reaction conditions, easiness in operation control, safety, reliability and low cost, and can lay a foundation for later industrial enlarged production.

Description

Technical Field

[0001] This invention relates to the field of chemical synthesis, and in particular to a method for preparing heterocyclic compounds. Background Technology

[0002] Heterocyclic compounds are widely present in drug molecules and profoundly influence their pharmacological properties. Even changing a single atom in a heterocycle can produce significant differences in previously similar analogs, highlighting the importance of heterocycles. Although various methods exist for the de novo synthesis of heterocyclic compounds, strategies for converting readily available carbocyclic rings into saturated heterocycles remain limited, often constrained by specific substrate requirements, customized synthetic routes, and restrictions on the types of heterocycles that can be constructed. Starting from readily available carbocyclic precursors and employing unconventional strategies to diversify heterocyclic structures would offer more strategically valuable preparation methods. Summary of the Invention

[0003] To address the above problems, the present invention provides a method for preparing the compound represented by formula (I), the method comprising: S1: Compound a1 or a2 undergoes reaction 1 in the presence of Lewis acid and H2O2, and the product undergoes reaction 2 in the presence of base to give compound b; S2: Compound b undergoes reaction 3 in the presence of chloride and catalyst, and the product undergoes reaction 4 to give the compound shown in formula (I);

[0004] in, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, halogen, alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxyl, nitro, and -OR. b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a-S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d Cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q1 groups; R1, R2 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally substituted by one or more Q2 groups; Or R4, R5 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally replaced by one or more Q3 groups; R6 is selected from ; R7 is selected from alkyl and aryl groups; wherein the alkyl and aryl groups are optionally substituted with one or more Q4 groups; A is selected from O, S, Se, Te, N-R8 and C(R9)(R 10 ); R8 is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q5 groups; R9, R 10 Each of the following is independently selected from alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxy, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl is optionally substituted by one or more Q6 groups; R' and R'' are each independently selected from alkyl groups, wherein the alkyl group is optionally replaced by one or more Q7 groups; Or R', R'' and the atoms attached thereto form a heterocyclic group, wherein the heterocyclic group is optionally replaced by one or more Q8; Q1, Q2, Q3, Q4, Q5, Q6, Q7, and Q8 are each independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano group, nitro group, hydroxyl group, amino group, carbonyl group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C6 alkenyl group, C2-C6 alkynyl group, and C6-C6 alkynyl group. 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, =NR a -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NRc S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q Replaced; Each time it appears, R Q Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q1 Replaced; Each time it appears, R Q1 Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12Cycloalkyl and 3-12 membered heterocyclic groups; Each time it appears, R a Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R b Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R c Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R d Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it occurs, the R x Each is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, 5-14 membered heteroaryl and C6-C 14 Aryl; n is 0, 1, 2, or 3.

[0005] The effects of the invention

[0006] This invention utilizes a bis(aromatic acyl peroxy) ketal intermediate to perform formal carbonyl substitution on a cyclic ketone, transforming a single cyclic ketone into multiple saturated heterocycles / carbon rings. Driven by electron-guided peroxy bond cleavage, this intermediate achieves double carbon-carbon bond cleavage of the cyclic ketone, generating an alkyl dichloride as a universal linker. This is then modularly introduced with simple nucleophiles to introduce nitrogen, oxygen, sulfur, selenium, tellurium, and carbon atoms. This method has a wide substrate applicability and high functional group tolerance, accelerating the synthesis of target molecules and enabling diverse post-modification of bioactive molecules. The method described in this invention avoids the generation of toxic substances, is environmentally friendly, simple, efficient, operates under mild conditions, is easy to control, safe, reliable, and low-cost, laying the foundation for subsequent industrial-scale production. Furthermore, the preparation method described in this invention achieves high reaction yields and high product purity. Detailed Implementation

[0007] To make the technical solution and beneficial effects of the present invention more apparent and understandable, a detailed description is provided below by listing specific embodiments. Unless otherwise defined, the technical and scientific terms used herein have the same meanings as those in the technical field to which this application pertains.

[0008] This invention provides a method for preparing a compound of formula (I), the method comprising: S1: Compound a1 or a2 undergoes reaction 1 in the presence of Lewis acid and H2O2, and the product undergoes reaction 2 in the presence of base to give compound b; S2: Compound b undergoes reaction 3 in the presence of chloride and catalyst, and the product undergoes reaction 4 to give the compound shown in formula (I);

[0009] in, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, halogen, alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxyl, nitro, and -OR. b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c Rd Cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q1 groups; R1, R2 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally substituted by one or more Q2 groups; Or R4, R5 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally replaced by one or more Q3 groups; R6 is selected from ; R7 is selected from alkyl and aryl groups; wherein the alkyl and aryl groups are optionally substituted with one or more Q4 groups; A is selected from O, S, Se, Te, N-R8 and C(R9)(R 10 ); R8 is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q5 groups; R9, R 10 Each of the following is independently selected from alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxy, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl is optionally substituted by one or more Q6 groups; R' and R'' are each independently selected from alkyl groups, wherein the alkyl group is optionally replaced by one or more Q7 groups; Or R', R'' and the atoms attached thereto form a heterocyclic group, wherein the heterocyclic group is optionally replaced by one or more Q8; Q1, Q2, Q3, Q4, Q5, Q6, Q7, and Q8 are each independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano group, nitro group, hydroxyl group, amino group, carbonyl group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C6 alkenyl group, C2-C6 alkynyl group, and C6-C6 alkynyl group. 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, =NR a -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NRc R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q Replaced; Each time it appears, R QEach group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SRa -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q1 Replaced; Each time it appears, R Q1 Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl and 3-12 membered heterocyclic groups; Each time it appears, R a Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R b Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R cSelected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R d Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it occurs, the R x Each is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, 5-14 membered heteroaryl and C6-C 14 Aryl; n is 0, 1, 2, or 3.

[0010] In some embodiments, R1 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a-S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0011] In some embodiments, R1 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OC(=O)OR b -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0012] In some embodiments, R2 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0013] In some embodiments, R2 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OC(=O)ORb -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0014] In some embodiments, R3 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a-NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0015] In some embodiments, R3 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OC(=O)OR b -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0016] In some embodiments, R4 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SRb -S(=O)R a -S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0017] In some embodiments, R4 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OC(=O)OR b -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0018] In some embodiments, R5 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0019] In some embodiments, R5 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a-OC(=O)OR b -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0020] In some embodiments, R1, R2 and the carbon atoms attached thereto form C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups.

[0021] In some embodiments, R1, R2 and the carbon atoms to which they are attached form C3-C8 cycloalkyl groups or 3-8 membered heterocyclic groups, wherein the 3-8 membered heterocyclic groups contain 1-4 heteroatoms selected from N, O, and S; In some embodiments, R4, R5, and the carbon atoms attached to them form C3-C. 12 Cycloalkyl, 3-12 membered heterocyclic groups.

[0022] In some embodiments, R4, R5 and the carbon atoms to which they are attached form C3-C8 cycloalkyl groups or 3-8 membered heterocyclic groups, wherein the 3-8 membered heterocyclic groups contain 1-4 heteroatoms selected from N, O, and S.

[0023] In some embodiments, the R7 is selected from C1-C6 alkyl and C6-C6 alkyl groups. 14 Aryl.

[0024] In some embodiments, the R7 is selected from C1-C4 alkyl and C6-C4 alkyl groups. 10 Aryl.

[0025] In some implementations, R6 is selected from... .

[0026] In some embodiments, R8 is selected from hydrogen, C1-C6 alkyl, C3-C6 alkyl, C4-C6 alkyl, C5-C6 alkyl, C6 ... 12Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0027] In some embodiments, R8 is selected from hydrogen, C1-C4 alkyl, C3-C8 cycloalkyl, 3-8 membered heterocyclic groups, C6-C4 cycloalkyl, C4-C5 cycloalkyl, C6-C5 ... 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0028] In some embodiments, R9 is selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxy, nitro, C3-C6 alkyl, hydroxyl, hydroxyl, and C3-C6 alkyl groups. 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0029] In some embodiments, R9 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0030] In some implementations, the R 10 Selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl compounds.

[0031] In some implementations, the R 10 Selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0032] In some embodiments, R' is selected from C1-C6 alkyl groups.

[0033] In some embodiments, R' is selected from C1-C4 alkyl groups.

[0034] In some embodiments, R'' is selected from C1-C6 alkyl groups.

[0035] In some embodiments, R'' is selected from C1-C4 alkyl groups.

[0036] In some implementations, R', R'' and the atoms they are attached to form a heterocyclic group containing two O atoms.

[0037] In some implementations, R', R'' and the atoms they are attached to form a 5-8 membered heterocyclic group containing two O atoms.

[0038] In some embodiments, Q1 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)ORb -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0039] In some embodiments, Q2 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)ORb -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0040] In some embodiments, Q3 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NRc C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0041] In some embodiments, Q4 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR cC(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0042] In some embodiments, Q5 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c Rd -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0043] In some embodiments, Q6 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR cC(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0044] In some embodiments, Q7 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c Rd -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0045] In some embodiments, Q8 is selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR cS(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0046] In some implementations, the R Q Selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d-NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0047] In some implementations, the R Q1 Each group is independently selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10-membered heteroaryl, C3-C8 cycloalkyl and 3-8-membered heterocyclic groups, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O and S.

[0048] In some implementations, the R a Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0049] In some implementations, the R bSelected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0050] In some implementations, the R c Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0051] In some implementations, the R d Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10 heteroaryl groups, wherein the 3-8 heterocyclic group and the 5-10 heteroaryl group contain 1-4 heteroatoms selected from N, O, and S.

[0052] In some implementations, the R x Each is independently selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, 3-8 heterocyclic, 5-10 heteroaryl, and C6-C 10 Aryl groups, wherein the 3-8 membered heterocyclic groups and 5-10 membered heteroaryl groups contain 1-4 heteroatoms selected from N, O, and S.

[0053] In some embodiments, in step S1, compound a1 or a2 undergoes reaction 1 in the presence of a Lewis acid and H2O2, and the product obtained after post-treatment reacts with... or Reaction 2 occurs, yielding compound b.

[0054] In some embodiments, the Lewis acid is selected from one or more of tin tetrachloride, tin dichloride, silver trifluoromethanesulfonate, silver bis(trifluoromethanesulfonyl)imide, zinc chloride, zinc bromide, titanium tetrachloride, ferric chloride, lithium chloride, magnesium chloride, and aluminum chloride.

[0055] In some embodiments, the Lewis acid is selected from tin dichloride.

[0056] In some embodiments, the base in step S1 is selected from organic or inorganic bases.

[0057] In some embodiments, the organic base is selected from one or more of triethylamine, 2,6-dimethylpyridine, pyridine, N,N-diisopropylethylamine, n-butyllithium, diisopropylaminolithium, sodium acetate, potassium acetate, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicycloundec-7-ene.

[0058] In some embodiments, the organic base is selected from 2,6-dimethylpyridine.

[0059] In some embodiments, the inorganic base is selected from one or more of potassium phosphate, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide.

[0060] In some embodiments, the reaction temperature of reaction 1 is 20-80°C.

[0061] In some embodiments, the reaction temperature of reaction 1 is 40-50°C.

[0062] In some embodiments, the reaction temperature of reaction 2 is 20-50°C.

[0063] In some embodiments, the reaction temperature of reaction 2 is room temperature.

[0064] In some implementations, the for .

[0065] In some implementations, the for .

[0066] In some embodiments, compound a1 or a2 with or The molar ratio is 1:1-5.

[0067] In some embodiments, compound a1 or a2 with or The molar ratio is 1:2.5.

[0068] In some embodiments, the chloride in step S2 is selected from one or more of lithium chloride, sodium chloride, potassium chloride, magnesium chloride, calcium chloride, ferric chloride, ferrous chloride, cobalt chloride, nickel chloride, copper chloride, cuprous chloride, zinc chloride, TMSCl, TESCl, and TBSCl.

[0069] In some embodiments, the chloride in step S2 is selected from TMSCl.

[0070] In some embodiments, the catalyst in step S2 is selected from one or more of iron salts, copper salts, ruthenium salts, nickel salts, and cobalt salts.

[0071] In some embodiments, the catalyst in step S2 is selected from one or more of FeCl3, FeCl2, FeSO4, Fe2(SO4)3, Fe(OAc)2, Fe(OAc)3, Fe(acac)2, Fe(acac)3, Fe(ClO4)3, CuCl2, CuCl, RuCl3, RuCl4, NiCl2, and CoCl2.

[0072] In some embodiments, the catalyst in step S2 is selected from FeCl3.

[0073] In some embodiments, the reaction temperature of reaction 3 is 20-50°C.

[0074] In some embodiments, the reaction temperature of reaction 3 is 25°C.

[0075] In some embodiments, the molar ratio of compound b to chloride in step S2 is 1:5-10.

[0076] In some embodiments, the molar ratio of compound b to chloride in step S2 is 1:7.

[0077] In some embodiments, when A is S, the reaction 4 is carried out in the presence of a sulfide or hydrosulfide to yield the product.

[0078] In some embodiments, the sulfide or hydrosulfide is selected from one or more of sodium sulfide, potassium sulfide, lithium sulfide, lithium hydrosulfide, sodium hydrosulfide, and potassium hydrosulfide.

[0079] In some embodiments, the sulfide or hydrosulfide is selected from sodium sulfide.

[0080] In some embodiments, the molar ratio of compound b to sulfide or hydrosulfide in step S2 is 1:2-7.

[0081] In some embodiments, the molar ratio of compound b to sulfide or hydrosulfide in step S2 is 1:5.

[0082] In some embodiments, when A is Se, reaction 4 is a reaction that occurs in the presence of a selenide or selenium hydride to yield the product.

[0083] In some embodiments, the selenide or selenide hydride is selected from one or more of sodium selenide, potassium selenide, lithium selenide, lithium selenide hydride, sodium selenide, potassium selenide, and tetrabutylammonium hydroselenate.

[0084] In some embodiments, the selenide or selenium hydride is selected from sodium selenide.

[0085] In some embodiments, the sodium selenide is obtained by in-situ preparation.

[0086] In some embodiments, the in-situ preparation method includes: mixing selenium powder with water to obtain a suspension, and then adding sodium borohydride and stirring.

[0087] In some embodiments, when A is Te, the reaction 4 is carried out in the presence of telluride or telluride hydride to yield the product.

[0088] In some embodiments, the telluride or telluride hydride is selected from one or more of sodium telluride, potassium telluride, lithium telluride, sodium telluride, and potassium telluride.

[0089] In some embodiments, the telluride or telluride hydride is selected from sodium telluride.

[0090] In some embodiments, the molar ratio of compound b to telluride or telluride hydride in step S2 is 1:2-7.

[0091] In some embodiments, the molar ratio of compound b to telluride or telluride hydride in step S2 is 1:5.

[0092] In some embodiments, when A is O, reaction 4 is a reaction with an aqueous solution of an inorganic base in the presence of a phase transfer catalyst to obtain the product.

[0093] In some embodiments, the phase transfer catalyst is selected from one or more of tetramethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium bisulfate, tetrabutylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide, and triphenylmethylphosphonium chloride.

[0094] In some embodiments, the phase transfer catalyst is selected from a mixture of tetrabutylammonium iodide and tetrabutylammonium hydrogen sulfate.

[0095] In some embodiments, the molar ratio of compound b to phase transfer catalyst in step S2 is 1:1-5.

[0096] In some embodiments, the molar ratio of compound b to phase transfer catalyst in step S2 is 1:2.

[0097] In some embodiments, the inorganic base is selected from one or more of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide.

[0098] In some embodiments, the inorganic base is selected from sodium hydroxide.

[0099] In some embodiments, when A is N-R8, reaction 4 is the product of reaction 3 reacting with H2N-R8 in the presence of iodide and base to obtain the product.

[0100] In some embodiments, the iodide is selected from sodium iodide, potassium iodide, lithium iodide, and tetrabutylammonium iodide.

[0101] In some embodiments, the iodide is selected from potassium iodide.

[0102] In some embodiments, the molar ratio of compound b to iodide in step S2 is 1:0.5-3.

[0103] In some embodiments, the molar ratio of compound b to iodide in step S2 is 1:1.

[0104] In some embodiments, the base is selected from organic or inorganic bases.

[0105] In some embodiments, the organic base is selected from one or more of triethylamine, 2,6-dimethylpyridine, pyridine, N,N-diisopropylethylamine, n-butyllithium, diisopropylaminolithium, sodium acetate, potassium acetate, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicycloundec-7-ene.

[0106] In some embodiments, the inorganic base is selected from one or more of potassium phosphate, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide.

[0107] In some embodiments, the inorganic base is selected from potassium carbonate.

[0108] In some embodiments, the molar ratio of compound b to base in step S2 is 1:2-7.

[0109] In some embodiments, the molar ratio of compound b to base in step S2 is 1:5.

[0110] In some embodiments, the molar ratio of compound b to H2N-R8 in step S2 is 1:2-7.

[0111] In some embodiments, the molar ratio of compound b to H2N-R8 in step S2 is 1:4.

[0112] In some implementations, when A is C(R9)(R 10 When ), reaction 4 is the product of reaction 3 reacting with CH2(R9)(R 10 The reaction proceeds to yield the product.

[0113] Terminology Explanation

[0114] Unless otherwise stated, the terms used in the specification and claims have the following meanings.

[0115] The term "alkyl" refers to a saturated aliphatic hydrocarbon group, which is a straight-chain or branched group containing 1 to 20 carbon atoms, preferably an alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12) carbon atoms, and more preferably an alkyl group containing 1 to 6 carbon atoms. Non-limiting examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, n-hexyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2-ethylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2,3-dimethylbutyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2, 3-Dimethylpentyl, 2,4-Dimethylpentyl, 2,2-Dimethylpentyl, 3,3-Dimethylpentyl, 2-Ethylpentyl, 3-Ethylpentyl, n-Octyl, 2,3-Dimethylhexyl, 2,4-Dimethylhexyl, 2,5-Dimethylhexyl, 2,2-Dimethylhexyl, 3,3-Dimethylhexyl, 4,4-Dimethylhexyl, 2-Ethylhexyl, 3-Ethylhexyl, 4-Ethylhexyl, 2-Methyl-2-Ethylpentyl, 2-Methyl-3-Ethylpentyl, n-Nonyl, 2-Methyl-2-Ethylhexyl, 2-Methyl-3-Ethylhexyl, 2,2-Diethylpentyl, n-Decyl, 3,3-Diethylhexyl, 2,2-Diethylhexyl, and their various branched isomers, etc. More preferably, lower alkyl groups containing 1 to 6 carbon atoms are used. Non-limiting examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, n-hexyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2-ethylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2,3-dimethylbutyl, etc. Alkyl groups can be substituted or unsubstituted, and when substituted, they can be substituted at any usable connection point. The substituents are preferably independently selected independently from one or more substituents chosen from the following: D atom, halogen, alkoxy, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclic oxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl.

[0116] The term "alkenyl" refers to an alkyl compound containing at least one carbon-carbon double bond in its molecule, wherein the definition of alkyl is as described above. Alkenyl groups can be substituted or unsubstituted, and when substituted, the substituent is preferably one or more of the following groups, independently selected from alkoxy, halogen, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclic oxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl substituents.

[0117] The term "alkynyl" refers to an alkyl compound containing at least one carbon-carbon triple bond in its molecule, wherein the definition of alkyl is as described above. The alkynyl group can be substituted or unsubstituted; when substituted, the substituent is preferably one or more of the following groups, independently selected from alkoxy, halogen, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclic oxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl substituents.

[0118] The term "cycloalkyl" refers to a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent, wherein the cycloalkyl ring contains 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 8 (e.g., 3, 4, 5, 6, 7, and 8) carbon atoms, and more preferably 3 to 6 carbon atoms. Non-limiting examples of monocyclic cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cyclohepttrienyl, cyclooctyl, etc.; polycyclic cycloalkyl groups include spirocyclic, fused-ring, and bridged-ring cycloalkyl groups.

[0119] The term "spirocycloalkyl" refers to a 5- to 20-membered polycyclic group that shares a single carbon atom (called a spiro atom) between its rings, and may contain one or more double bonds. Preferably, it is 6- to 14-membered, more preferably 7- to 10-membered (e.g., 7, 8, 9, or 10-membered). Spirocycloalkyl groups are classified as monospirocycloalkyl, bispirocycloalkyl, or polyspirocycloalkyl groups based on the number of shared spiro atoms between the rings, with monospirocycloalkyl and bispirocycloalkyl groups being preferred. More preferably, it is a 3 / 5-membered, 3 / 6-membered, 4 / 4-membered, 4 / 5-membered, 4 / 6-membered, 5 / 5-membered, or 5 / 6-membered monospirocycloalkyl group. Non-limiting examples of spirocycloalkyl groups include: .

[0120] The term "fused cycloalkyl" refers to a 5- to 20-membered polycyclic aromatic hydrocarbon group in which each ring in the system shares an adjacent pair of carbon atoms with other rings in the system, wherein one or more rings may contain one or more double bonds. Preferably, it is 6- to 14-membered, more preferably 7- to 10-membered (e.g., 7, 8, 9, or 10-membered). Depending on the number of constituent rings, it can be classified as bicyclic, tricyclic, tetracyclic, or polycyclic fused cycloalkyl, preferably bicyclic or tricyclic, more preferably 3 / 4-membered, 3 / 5-membered, 3 / 6-membered, 4 / 4-membered, 4 / 5-membered, 4 / 6-membered, 5 / 4-membered, 5 / 5-membered, 5 / 6-membered, 6 / 3-membered, 6 / 4-membered, 6 / 5-membered, and 6 / 6-membered bicyclic alkyl groups. Non-limiting examples of fused cycloalkyl groups include: .

[0121] The term "bridged cycloalkyl" refers to a 5- to 20-membered, all-carbon polycyclic group in which any two rings share two non-directly bonded carbon atoms, and may contain one or more double bonds. Preferably, it is 6- to 14-membered, more preferably 7- to 10-membered (e.g., 7, 8, 9, or 10-membered). Depending on the number of constituent rings, it can be classified as bicyclic, tricyclic, tetracyclic, or polycyclic bridged cycloalkyl, preferably bicyclic, tricyclic, or tetracyclic, more preferably bicyclic or tricyclic. Non-limiting examples of bridged cycloalkyl groups include:

[0122] The cycloalkyl ring comprises a cycloalkyl group (including monocyclic, spirocyclic, fused, and bridged rings) fused to an aryl, heteroaryl, or heterocyclic alkyl ring as described above, wherein the ring attached to the parent structure is a cycloalkyl group. Non-limiting examples include... , , etc.; preferred and .

[0123] The cycloalkyl group can be substituted or unsubstituted, and when substituted, it can be substituted at any usable connection point. The substituent is preferably selected independently from one or more substituents selected from halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclic oxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl and heteroaryl.

[0124] The term "alkoxy" refers to -O-(alkyl) and -O-(cycloalkyl), where alkyl and cycloalkyl are defined as described above. Non-limiting examples of alkoxy groups include methoxy, ethoxy, propoxy, and butoxy. Alkoxy groups can be optionally substituted or unsubstituted, and when substituted, they are preferably one or more of the following groups, independently selected from D atoms, halogens, alkoxy groups, haloalkyl groups, haloalkoxy groups, cycloalkyloxy groups, heterocyclic oxy groups, hydroxyl groups, hydroxyalkyl groups, cyano groups, amino groups, nitro groups, cycloalkyl groups, heterocyclic groups, aryl groups, and heteroaryl groups.

[0125] The term "heterocyclic group" refers to a saturated or partially unsaturated monocyclic or polycyclic substituent containing 3 to 20 ring atoms, wherein one or more ring atoms are heteroatoms selected from nitrogen, oxygen, and sulfur, wherein the sulfur may optionally be oxidized (i.e., forming sulfoxide or sulfone), but excluding the -OO-, -OS-, or -SS- ring moiety, and the remaining ring atoms are carbon. Preferably, it contains 3 to 12 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12) ring atoms, wherein 1 to 4 (e.g., 1, 2, 3, and 4) are heteroatoms; more preferably, it contains 3 to 8 ring atoms (e.g., 3, 4, 5, 6, 7, and 8), wherein 1 to 3 (e.g., 1, 2, and 3) are heteroatoms; even more preferably, it contains 3 to 6 ring atoms, wherein 1 to 3 are heteroatoms; most preferably, it contains 5 or 6 ring atoms, wherein 1 to 3 are heteroatoms. Non-limiting examples of monocyclic heterocyclic groups include pyrrolidinyl, tetrahydropyranyl, 1,2,3,6-tetrahydropyridyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, and homopiperazinyl. Polycyclic heterocyclic groups include spirocyclic, fused-ring, and bridged-ring heterocyclic groups.

[0126] The term "spiroheterocyclic group" refers to a 5- to 20-membered polycyclic heterocyclic group in which one or more ring atoms share a single atom (called a spiro atom), wherein the sulfur may optionally be oxidized (i.e., forming a sulfoxide or sulfone), and the remaining ring atoms are carbon. It may contain one or more double bonds. Preferably, it is 6 to 14-membered, more preferably 7 to 10-membered (e.g., 7, 8, 9, or 10-membered). Spiroheterocyclic groups are classified into monospirocyclic, bispirocyclic, or polyspirocyclic groups according to the number of shared spiro atoms between rings, with monospirocyclic and bispirocyclic groups being preferred. More preferably, it is a 3 / 5-membered, 3 / 6-membered, 4 / 4-membered, 4 / 5-membered, 4 / 6-membered, 5 / 5-membered, or 5 / 6-membered monospirocyclic group. Non-limiting examples of spirocyclic groups include: .

[0127] The term "fused heterocyclic group" refers to a 5- to 20-membered polycyclic heterocyclic group in which each ring in the system shares an adjacent pair of atoms with other rings in the system. One or more rings may contain one or more double bonds, wherein one or more ring atoms are heteroatoms selected from nitrogen, oxygen, and sulfur, wherein the sulfur may optionally be oxidized (i.e., forming sulfoxide or sulfone), and the remaining ring atoms are carbon. Preferably, it is 6- to 14-membered, more preferably 7- to 10-membered (e.g., 7, 8, 9, or 10-membered). Depending on the number of constituent rings, it can be classified as bicyclic, tricyclic, tetracyclic, or polycyclic fused heterocyclic groups, preferably bicyclic or tricyclic, more preferably 3-membered / 4-membered, 3-membered / 5-membered, 3-membered / 6-membered, 4-membered / 4-membered, 4-membered / 5-membered, 4-membered / 6-membered, 5-membered / 4-membered, 5-membered / 5-membered, 5-membered / 6-membered, 6-membered / 3-membered, 6-membered / 4-membered, 6-membered / 5-membered, and 6-membered / 6-membered bicyclic fused heterocyclic groups. Non-limiting examples of fused heterocyclic groups include:

[0128] and .

[0129] The term "bridged heterocyclic group" refers to a 5- to 14-membered polycyclic heterocyclic group in which any two rings share two non-directly bonded atoms. It may contain one or more double bonds, wherein one or more ring atoms are heteroatoms selected from nitrogen, oxygen, and sulfur, wherein the sulfur may optionally be oxidized (i.e., forming sulfoxide or sulfone), and the remaining ring atoms are carbon. Preferably, it is 6- to 14-membered, more preferably 7- to 10-membered (e.g., 7, 8, 9, or 10-membered). Depending on the number of rings, it can be classified as bicyclic, tricyclic, tetracyclic, or polycyclic bridged heterocyclic groups, preferably bicyclic, tricyclic, or tetracyclic, more preferably bicyclic or tricyclic. Non-limiting examples of bridged heterocyclic groups include: .

[0130] The heterocyclic ring comprises a heterocyclic group (including monocyclic, spirocyclic, fused heterocyclic, and bridged heterocyclic rings) fused to an aryl, heteroaryl, or cycloalkyl ring as described above, wherein the ring connected to the parent structure is a heterocyclic group, and non-limiting examples include: and wait.

[0131] The heterocyclic group can be substituted or unsubstituted. When substituted, it can be substituted at any usable connection point. The substituent is preferably selected independently from one or more substituents selected from halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclicoxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl and heteroaryl.

[0132] The term "aryl" refers to a 6- to 14-membered all-carbon monocyclic or fused polycyclic (fused polycyclic) group having a conjugated π-electron system, preferably 6- to 10-membered, such as phenyl and naphthyl. The aryl ring comprises an aryl ring fused to a heteroaryl, heterocyclic, or cycloalkyl ring as described above, wherein the ring attached to the parent structure is an aryl ring, and non-limiting examples include: and .

[0133] The aryl group can be substituted or unsubstituted. When substituted, it can be substituted at any usable linker. The substituent is preferably independently selected independently from one or more substituents chosen from halogens, alkyl groups, alkoxy groups, haloalkyl groups, haloalkoxy groups, cycloalkyloxy groups, heterocyclic oxy groups, hydroxy groups, hydroxyalkyl groups, cyano groups, amino groups, nitro groups, cycloalkyl groups, heterocyclic groups, aryl groups, and heteroaryl groups. The term "heteroaryl" refers to a heteroaromatic system comprising 1 to 4 (e.g., 1, 2, 3, and 4) heteroatoms and 5 to 14 ring atoms, wherein the heteroatoms are selected from oxygen, sulfur, and nitrogen. The heteroaryl group is preferably 5 to 10-membered (e.g., 5, 6, 7, 8, 9, or 10-membered), more preferably 5- or 6-membered, such as furanyl, thiophene, pyridinyl, pyrroleyl, N-alkylpyrroleyl, pyrimidinyl, pyrazinyl, pyridazinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, etc. The heteroaryl ring comprises a heteroaryl group fused to an aryl, heterocyclic, or cycloalkyl ring as described above, wherein the ring connected to the parent structure is a heteroaryl ring, and non-limiting examples include: and .

[0134] The heteroaryl group can be substituted or unsubstituted. When substituted, it can be substituted at any usable connection point. The substituent is preferably selected independently from one or more substituents selected from halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, cycloalkyloxy, heterocyclic oxy, hydroxy, hydroxyalkyl, cyano, amino, nitro, cycloalkyl, heterocyclic, aryl and heteroaryl.

[0135] The aforementioned cycloalkyl, heterocyclic, aryl, and heteroaryl groups include residues derived from removing one hydrogen atom from a parent ring atom, or residues derived from removing two hydrogen atoms from the same or two different ring atoms of the parent, namely "divalent cycloalkyl", "divalent heterocyclic", "aryl", and "heteroaryl".

[0136] The term "hydroxyalkyl" refers to an alkyl group that is replaced by one or more hydroxyl groups, wherein the alkyl group is as defined above.

[0137] The term "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0138] The term "hydroxyl group" refers to -OH.

[0139] The term "thiol" refers to -SH.

[0140] The term "amino" refers to -NH2.

[0141] The term "cyano" refers to -CN.

[0142] The term "nitro" refers to -NO2.

[0143] The term "oxo" or "oxo" refers to "=O".

[0144] The term "carboxyl group" refers to -C(O)OH.

[0145] "Optional" or "optionally" means that the event or environment described below may but does not have to occur, and the description includes the possibility or absence of the event or environment. For example, "optionally alkyl-substituted heterocyclic group" means that the alkyl group may but does not have to be present, and the description includes cases where the heterocyclic group is substituted with an alkyl group and cases where the heterocyclic group is not substituted with an alkyl group.

[0146] "Substituted" refers to one or more hydrogen atoms in a group, preferably 1 to 5, more preferably 1 to 3 hydrogen atoms, which are independently substituted by the corresponding number of substituents. Those skilled in the art can determine possible or impossible substitutions without much effort (through experimentation or theory). For example, an amino or hydroxyl group with free hydrogen may be unstable when combined with a carbon atom having an unsaturated bond (such as an alkene).

[0147] The method of the present invention will be described below through specific embodiments. It should be understood that these embodiments are used to illustrate the basic principles, main features and advantages of the present invention, and the present invention is not limited to the scope of the following embodiments. The implementation conditions used in the embodiments can be further adjusted according to specific requirements, and the implementation conditions not specified are usually the conditions in conventional experiments.

[0148] The following examples 1 The 1H NMR spectra were obtained using a Bruker instrument (400 MHz), and chemical shifts are expressed in ppm. Tetramethylsilane internal standard (0.00 ppm) was used. 1 H NMR representation: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broadened, dd = doublet of doublet, dt = doublet of triplet. If the coupling constant is provided, the unit is Hz.

[0149] The mass spectrometry results were obtained using an LC / MS instrument, with ESI as the ionization method.

[0150] In the following examples, unless otherwise specified, all temperatures are in Celsius; unless otherwise specified, all starting materials and reagents are commercially available or synthesized according to known methods; commercially available materials and reagents are used directly without further purification; unless otherwise specified, commercially available manufacturers include, but are not limited to, Sinopharm Group, Bailingwei Technology Co., Ltd., TCI (Shanghai) Chemical Industry Development Co., Ltd., Shanghai Bid Pharmaceutical Technology Co., Ltd., and Shanghai Mairui Chemical Technology Co., Ltd.

[0151] Unless otherwise specified in the examples, the solution in the reaction refers to an aqueous solution.

[0152] Unless otherwise specified in the examples, the reaction temperature is room temperature, which is 20℃-30℃.

[0153] The reaction process in the examples was monitored using thin-layer chromatography (TLC). The developing solvent used in the reaction, the eluent system used for column chromatography to purify the compounds, or the developing solvent system for TLC included: A: petroleum ether and ethyl acetate system; B: dichloromethane and methanol system; C: n-hexane: ethyl acetate. The volume ratio of the solvent varied depending on the polarity of the compound and could also be adjusted by adding a small amount of acidic or basic reagents, such as acetic acid or triethylamine.

[0154] Example 1: Preparation of Compound 2

[0155] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S1 To a 100 mL reaction flask equipped with a magnetic stirrer, ketone 1 (3 mmol), acetonitrile (12 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially. The reaction mixture was stirred at 40 °C for 29 hours, and the progress was monitored by TLC. After the reaction, the mixture was diluted with 1:1 diethyl ether / ethyl acetate (60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with 1:1 diethyl ether / ethyl acetate (3 × 60 mL). The organic layers were combined, washed with water, and the aqueous phase was extracted again with a 1:1 mixture. All organic layers were combined, washed with saturated brine, dried over anhydrous Na2SO4, filtered, concentrated, and further concentrated under high vacuum for 1 hour. The residue was dissolved in EtOAc (30 mL), cooled to -20 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The mixture was allowed to slowly rise to room temperature naturally and stirred for 2 hours. The mixture was then washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give compound S1 as a white solid (1.92 g, 91% yield). 1 H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.38 (s, 2H), 8.13 (s, 1H), 8.11 (s, 1H), 7.39 – 7.31 (m, 2H), 7.29 – 7.26 (m, 2H), 7.25 – 7.23 (m, 1H), 3.05 (tt, J= 12.9, 3.5Hz, 1H), 2.63 (d, J = 13.9 Hz, 1H), 2.55 (d, J = 10.9 Hz, 1H), 2.12 – 2.00 (m, 3H), 2.00 – 1.81 (m, 2H), 1.70 – 1.53 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ161.56, 161.42, 144.35, 132.88 (q, J = 34.3 Hz), 132.80 (q, J = 34.3 Hz),129.74 – 129.50 (m), 129.44, 129.35, 128.93, 127.50 – 127.24 (m), 127.05,126.94, 122.75 (q, J = 273.1 Hz), 113.95, 40.41, 37.31, 33.03, 29.85, 22.53. 19 F NMR (565 MHz, CDCl3) δ -63.03 (s, 6F), -63.05 (s, 6F). HRMS: Chemical formula ([M]): C 30 H 20 F 12 O6, calculated value 722.1407 [M+NH4] + Measured value: 722.1396. Step 2: Synthesis of Compound 2 Add bisperoxide S1 (0.2 mmol, 1.0 equivalent) to an 8 mL reaction flask. Transfer to a glove box and add 1,4-dioxane (1.6 mL), TMSCl (1.4 mmol, 152.1 mg, 7.0 equivalent), and 0.1 M FeCl3 solution (0.04 mmol, 0.4 mL). Stir at 25 °C for 24 hours. After evaporating the solvent, add sodium sulfide (Na2S, 1.0 mmol, 78 mg, 5.0 equivalent), DMF (1.6 mL), and deoxygenated water (0.8 mL) to the glove box. Stir at 80 °C for 24 hours. Cool, add water, extract with diethyl ether, dry and concentrate, and then chromatographically obtain compound 2 as a colorless liquid (24.4 mg, 68% yield). Characterization data: 1H NMR (400 MHz, CDCl3) δ 7.31 (t, J = 7.6 Hz, 2H), 7.24 – 7.16 (m, 3H), 2.91 (ddd, J = 11.7, 8.7, 3.1 Hz, 1H), 2.80 (dd, J= 13.0, 11.6 Hz, 1H), 2.70 (td, J = 12.9, 2.8 Hz, 1H), 2.64 (dd, J = 13.1,2.9 Hz, 1H), 2.59 (dt, J = 13.5, 1.8 Hz, 1H), 2.21 – 2.15 (m, 1H), 2.04 –1.99 (m, 1H), 1.91 – 1.82 (m, 1H), 1.62 – 1.54 (m, 1H). 13 C10 NMR (151 MHz, CDCl3) δ 146.60, 128.70, 126.86, 126.63, 45.36, 35.18, 33.74, 28.63, 28.48. HRMS: Chemical formula ([M]): C10 11 H 14 S, calculated value 179.0889 [M+H]+, measured value: 179.0886.

[0156] Example 2 Preparation of Compound 3

[0157] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S1 To a 100 mL reaction flask equipped with a magnetic stirrer, ketone 1 (3 mmol), acetonitrile (12 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially. The reaction mixture was stirred at 40 °C for 29 hours, and the progress was monitored by TLC. After the reaction, the mixture was diluted with 1:1 diethyl ether / ethyl acetate (60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with 1:1 diethyl ether / ethyl acetate (3 × 60 mL). The organic layers were combined, washed with water, and the aqueous phase was extracted again with a 1:1 mixture. All organic layers were combined, washed with saturated brine, dried over anhydrous Na2SO4, filtered, concentrated, and further concentrated under high vacuum for 1 hour. The residue was dissolved in EtOAc (30 mL), cooled to -20 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The mixture was allowed to slowly rise to room temperature naturally and stirred for 2 hours. The mixture was then washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give compound S1 as a white solid (1.92 g, 91% yield). 1 H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.38 (s, 2H), 8.13 (s, 1H), 8.11 (s, 1H), 7.39 – 7.31 (m, 2H), 7.29 – 7.26 (m, 2H), 7.25 – 7.23 (m, 1H), 3.05 (tt, J = 12.9, 3.5Hz, 1H), 2.63 (d, J = 13.9 Hz, 1H), 2.55 (d, J = 10.9 Hz, 1H), 2.12 – 2.00 (m, 3H), 2.00 – 1.81 (m, 2H), 1.70 – 1.53 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ161.56, 161.42, 144.35, 132.88 (q, J = 34.3 Hz), 132.80 (q,J = 34.3 Hz),129.74 – 129.50 (m), 129.44, 129.35, 128.93, 127.50 – 127.24 (m), 127.05,126.94, 122.75 (q, J = 273.1 Hz), 113.95, 40.41, 37.31, 33.03, 29.85, 22.53. 19 F NMR (565 MHz, CDCl3) δ -63.03 (s, 6F), -63.05 (s, 6F). HRMS: Chemical formula ([M]): C 30 H 20 F 12 O6, calculated value 722.1407 [M+NH4] + Measured value: 722.1396.

[0158] Step 2: Synthesis of Compound 3. S1 (0.2 mmol, 140.8 mg, 1.0 equivalent) was added to an 8 mL reaction flask. The mixture was then transferred to a glove box, and 1,4-dioxane (1.6 mL), TMSCl (1.4 mmol, 152.1 mg, 7.0 equivalent), and 0.1 M FeCl3 solution (0.04 mmol, 0.4 mL) were added. The mixture was stirred at 25 °C for 24 hours. After evaporating the solvent, a pre-prepared monodeprotonated 2-(4-methoxyphenyl)acetonitrile 2-MeTHF / THF solution (1 mmol, 1 mL) was added to the glove box, and the mixture was stirred at 80 °C for 24 hours. Cooling and dilution chromatography yielded carbocyclic product 3 (combined yield 94%). Characterization data (major isomers): 1 H NMR (600 MHz, CDCl3) δ 7.43 (d, J = 8.2 Hz, 2H), 7.34 – 7.30(m, 2H), 7.26 – 7.21 (m, 3H), 6.91 (d, J = 8.3 Hz, 2H), 3.81 (s, 3H), 3.15(t, J = 12.4 Hz, 1H), 2.32 (d, J = 12.4 Hz, 1H), 2.25 (d, J = 13.4 Hz, 1H), 2.09 – 2.02 (m, 3H), 1.86 (t, J = 12.9 Hz, 1H), 1.83 – 1.77 (m, 1H), 1.55 –1.48 (m, 1H). 13C NMR (151 MHz, CDCl3) δ 159.29, 145.24, 133.22, 128.79,127.02, 126.81, 126.71, 114.36, 55.49, 44.88, 44.18, 41.57, 37.03, 32.81,24.03. HRMS:C 20 H 21 NO, calculated value 309.1961 [M+NH4]+, measured value: 309.1958.

[0159] Example 3 Preparation of Compound 5

[0160] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S2 Ketone 4 (3 mmol), acetonitrile (1.5 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 50 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target precursor compound S2 as a white solid (1.92 g, yield 86%).1 H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.37(s, 2H), 8.14 (s, 2H), 7.39 – 7.34 (m, 1H), 7.31 – 7.26 (m, 3H), 2.72 – 2.64(m, 5H), 2.64 – 2.49 (m, 4H), 2.30 (td, J = 13.8, 3.8 Hz, 2H). 13 C NMR (151MHz, CDCl3) δ 161.36, 161.17, 136.70, 135.84, 133.33, 132.94 (q, J = 34.5Hz), 132.90 (q, J = 34.4 Hz), 129.61 (q, J = 3.7 Hz), 129.21, 129.09, 128.73,127.68 – 127.38 (m), 126.98, 124.98, 122.74 (q, J = 273.1 Hz), 122.70 (q, J =273.1 Hz), 121.00, 111.57, 41.22, 31.67, 27.66, 21.30. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 12F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 21 F 12 NO6, [M+Na]+ Calculated value: 766.1069, Measured value: 766.1069.

[0161] Step 2: Synthesis of Compound 5 To an 8 mL reaction flask equipped with a magnetic stirrer and oven-dried, 0.1 mmol (1.0 equivalence) of purified bisperoxide S2 (column-peroxide purified by column chromatography) was added. The flask was transferred to a nitrogen glove box, and 0.8 mL of 1,4-dioxane was added, followed by trimethylchlorosilane (TMSCl, 0.7 mmol, 76.1 mg, 7.0 equivalence) and 0.1 M ferric chloride (FeCl3) dioxane stock solution (0.02 mmol, 0.2 mL, 20 mol%). The flask was sealed and removed from the glove box, and the reaction was stirred at 25 °C for 24 hours (600 rpm). Subsequently, the solvent was removed by rotary evaporation. Outside the glove box, tetrabutylammonium iodide (TBAI, 0.1 mmol, 36.9 mg, 1.0 equivalent) and tetrabutylammonium hydrogen sulfate (TBAHSO4, 0.1 mmol, 34.0 mg, 1.0 equivalent) were added to the reaction flask. The flask was then returned to the nitrogen glove box, and an aqueous sodium hydroxide solution (20 wt%, 1.2 mL) was added. The flask was sealed and removed from the glove box, placed on an aluminum heating block preheated to 80 °C, and stirred at 80 °C for 24 hours (600 rpm). After cooling the reaction mixture to room temperature, it was extracted with diethyl ether (4 × 2.5 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the target oxyheterocyclic product compound 5 as a white solid (15.4 mg, 76% separation yield). (Note: The overall yield of the two-step conversion from the starting ketone to 5 was 65%). Characterization data: Rf = 0.4 (16% v / v ethyl acetate / n-hexane). 1 H NMR (600MHz, CDCl3) δ 7.29 – 7.23 (m, 4H), 4.09 (dd, J = 12.4, 4.2 Hz, 2H), 3.99 (t,J = 12.1 Hz, 2H), 2.65 (s, 3H), 2.29 (d, J = 13.4 Hz, 2H), 2.10 (td, J =12.8, 3.6 Hz, 2H). 13 C10 NMR (151 MHz, CDCl3) δ 136.76, 136.61, 133.08, 128.27, 126.69, 124.86, 121.37, 64.69, 39.55, 35.38, 21.08. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H15 NO, calculated value 202.1226 [M+H]+, measured value: 202.1225.

[0162] Example 4 Preparation of Compound 6

[0163] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S2 Ketone 4 (3 mmol), acetonitrile (1.5 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 50 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target precursor compound S2 as a white solid (1.92 g, yield 86%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.37(s, 2H), 8.14 (s, 2H), 7.39 – 7.34 (m, 1H), 7.31 – 7.26 (m, 3H), 2.72 – 2.64(m, 5H), 2.64 – 2.49 (m, 4H), 2.30 (td, J = 13.8, 3.8 Hz, 2H). 13 C NMR (151MHz, CDCl3) δ 161.36, 161.17, 136.70, 135.84, 133.33, 132.94 (q, J = 34.5Hz), 132.90 (q, J = 34.4 Hz), 129.61 (q, J = 3.7 Hz), 129.21, 129.09, 128.73,127.68 – 127.38 (m), 126.98, 124.98, 122.74 (q, J = 273.1 Hz), 122.70 (q, J =273.1 Hz), 121.00, 111.57, 41.22, 31.67, 27.66, 21.30. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 12F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 21 F 12 NO6, [M+Na]+ Calculated value: 766.1069, Measured value: 766.1069.

[0164] Step 2: Synthesis of Compound 6 To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, 0.1 mmol (1.0 equivalent) of bisperoxide S2 purified by column chromatography was added. The flask was transferred to a nitrogen glove box, and 0.8 mL of 1,4-dioxane was added, followed by trimethylchlorosilane (TMSCl, 0.7 mmol, 76.1 mg, 7.0 equivalent) and 0.1 M ferric chloride (FeCl3) dioxane stock solution (0.02 mmol, 0.2 mL, 20 mol%). The flask was sealed and removed from the glove box, and the reaction was stirred at 25 °C for 24 hours (600 rpm). Subsequently, the solvent was removed by rotary evaporation. Outside the glove box, potassium iodide (KI, 0.1 mmol, 16.6 mg, 1.0 equivalent) and potassium carbonate (K₂CO₃, 0.5 mmol, 69.1 mg, 5.0 equivalent) were added to the reaction flask. The flask was then returned to the nitrogen glove box, and acetonitrile (0.4 mL) and benzylamine (0.4 mmol, 4.0 equivalent) were added. The flask was sealed and removed from the glove box, placed on an aluminum heating block preheated to 80 °C, and stirred at 80 °C for 24 hours (600 rpm). After cooling the reaction mixture to room temperature, it was diluted with diethyl ether (2 mL), filtered through a short silica gel column, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the target nitrogen heterocyclic product compound 6 as a white solid (15.5 mg, 53% separation yield). (Note: The overall yield of the two-step conversion from the starting ketone to 6 was 46%). Characterization data: Rf = 0.4 (16% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.43 – 7.31 (m, 4H), 7.30– 7.26 (m, 2H), 7.25 – 7.17 (m, 3H), 3.61 (s, 2H), 3.15 – 2.91 (m, 2H), 2.71– 2.55 (m, 5H), 2.36 – 2.28 (m, 2H), 2.15 – 1.99 (m, 2H). 13C10 NMR (151 MHz, CDCl3) δ 138.21, 137.18, 136.75, 132.91, 129.15, 128.38, 128.06, 127.24, 126.55, 124.91, 121.75, 62.85, 50.40, 40.26, 34.96, 21.18. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 20 H 22 N2, calculated value 291.1856 [M+H]+, measured value: 291.1852.

[0165] Example 5 Preparation of Compound 7

[0166] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S2 Ketone 4 (3 mmol), acetonitrile (1.5 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 50 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target precursor compound S2 as a white solid (1.92 g, yield 86%). 1 H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.37(s, 2H), 8.14 (s, 2H), 7.39 – 7.34 (m, 1H), 7.31 – 7.26 (m, 3H), 2.72 – 2.64(m, 5H), 2.64 – 2.49 (m, 4H), 2.30 (td, J = 13.8, 3.8 Hz, 2H). 13C NMR (151MHz, CDCl3) δ 161.36, 161.17, 136.70, 135.84, 133.33, 132.94 (q, J = 34.5Hz), 132.90 (q, J = 34.4 Hz), 129.61 (q, J = 3.7 Hz), 129.21, 129.09, 128.73,127.68 – 127.38 (m), 126.98, 124.98, 122.74 (q, J = 273.1 Hz), 122.70 (q, J =273.1 Hz), 121.00, 111.57, 41.22, 31.67, 27.66, 21.30. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 12F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 21 F 12 NO6, [M+Na]+ Calculated value: 766.1069, Measured value: 766.1069.

[0167] Step 2: Synthesis of Compound 7 To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, 0.1 mmol (1.0 equivalent) of bisperoxide S2 purified by column chromatography was added. The flask was transferred to a nitrogen glove box, and 0.8 mL of 1,4-dioxane was added, followed by trimethylchlorosilane (TMSCl, 0.7 mmol, 76.1 mg, 7.0 equivalent) and 0.1 M ferric chloride (FeCl3) dioxane stock solution (0.02 mmol, 0.2 mL, 20 mol%). The flask was sealed and removed from the glove box, and the reaction was stirred at 25 °C for 24 hours (600 rpm). Subsequently, the solvent was removed by rotary evaporation. The reaction flask was returned to the nitrogen glove box, and sodium sulfide (Na₂S, 0.5 mmol, 39.0 mg, 5.0 equivalence), N,N-dimethylformamide (DMF, 0.8 mL), and deoxygenated water (0.4 mL) were added. The flask was sealed and removed from the glove box, placed on an aluminum heating block preheated to 80 °C, and stirred at 80 °C for 24 hours (600 rpm). After cooling the reaction mixture to room temperature, it was diluted with deionized water (5 mL) and extracted with diethyl ether (4 × 2.5 mL). The combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the target sulfur heterocyclic product compound 7 as a white solid (12.1 mg, 56% yield). (Note: The total yield of the two-step conversion from the starting ketone to 7 was 48%). Characterization data: Rf = 0.6 (5% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.32 – 7.28 (m, 1H), 7.26 – 7.22 (m, 3H), 3.32 (ddd, J = 14.9, 12.7, 2.2 Hz, 2H), 2.74 – 2.68 (m, 2H), 2.64 (s, 3H), 2.59 (dtd, J = 12.8, 3.6, 1.7 Hz, 2H), 2.18 (ddd, J = 13.6, 12.5, 3.1 Hz, 2H). 13 C10 NMR (151 MHz, CDCl3) δ 137.50, 136.23, 133.15, 128.19, 126.75, 124.96, 121.03, 41.81, 36.79, 25.54, 21.31. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H15 NS, calculated value 218.0998 [M+H]+, measured value: 218.0992.

[0168] Example 6 Preparation of Compound 8

[0169] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S2 Ketone 4 (3 mmol), acetonitrile (1.5 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 50 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target precursor compound S2 as a white solid (1.92 g, yield 86%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.37(s, 2H), 8.14 (s, 2H), 7.39 – 7.34 (m, 1H), 7.31 – 7.26 (m, 3H), 2.72 – 2.64(m, 5H), 2.64 – 2.49 (m, 4H), 2.30 (td, J = 13.8, 3.8 Hz, 2H). 13 C NMR (151MHz, CDCl3) δ 161.36, 161.17, 136.70, 135.84, 133.33, 132.94 (q, J = 34.5Hz), 132.90 (q, J = 34.4 Hz), 129.61 (q, J = 3.7 Hz), 129.21, 129.09, 128.73,127.68 – 127.38 (m), 126.98, 124.98, 122.74 (q, J = 273.1 Hz), 122.70 (q, J =273.1 Hz), 121.00, 111.57, 41.22, 31.67, 27.66, 21.30. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 12F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 21 F 12 NO6, [M+Na]+ Calculated value: 766.1069, Measured value: 766.1069.

[0170] Step 2: Synthesis of Compound 8 To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, 0.1 mmol (1.0 equivalent) of purified bisperoxide S2 (column-peroxide purified by column chromatography) was added. The flask was transferred to a nitrogen glove box, and 0.8 mL of 1,4-dioxane was added, followed by trimethylchlorosilane (TMSCl, 0.7 mmol, 76.1 mg, 7.0 equivalent) and 0.1 M ferric chloride (FeCl3) dioxane stock solution (0.02 mmol, 0.2 mL, 20 mol%). The flask was sealed and removed from the glove box, and the reaction was stirred at 25 °C for 24 hours (600 rpm). Subsequently, the solvent was removed by rotary evaporation. The reaction flask was returned to the nitrogen glove box, and N,N-dimethylformamide (DMF, 0.8 mL) and an aqueous solution or suspension of sodium selenide (NaHSe) prepared in situ were added (in situ preparation method: 0.5 mmol of Se powder was mixed with 0.8 mL of deoxygenated water to form a suspension, and 38.0 mg of NaBH4 was added in portions while stirring for 2 hours). The reaction flask was sealed and removed from the glove box, placed on an aluminum heating block preheated to 80 °C, and stirred at 80 °C for 24 hours (600 rpm). After the reaction mixture was cooled to room temperature, it was diluted with deionized water (5 mL) and extracted with diethyl ether (4 × 2.5 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the target selenium heterocyclic product compound 8 as a white solid (23.2 mg, 88% yield). (Note: The overall yield of the two-step conversion from the starting ketone to 8 is 76%). Characterization data: Rf = 0.6 (5% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.33 – 7.28 (m,1H), 7.27 – 7.20 (m, 3H), 3.42 (t, J = 12.9 Hz, 2H), 2.80 – 2.56 (m, 7H), 2.31 (t, J = 13.1 Hz, 2H). 13 C10 NMR (151 MHz, CDCl3) δ 137.93, 136.13, 133.16, 128.14, 126.74, 124.98, 120.81, 42.61, 37.37, 21.38, 16.08. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H 15NSe, calculated value 266.0442 [M+H]+, measured value: 266.0451.

[0171] Example 7 Preparation of Compound 9

[0172] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S2 Ketone 4 (3 mmol), acetonitrile (1.5 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 50 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target precursor compound S2 as a white solid (1.92 g, yield 86%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 2H), 8.37(s, 2H), 8.14 (s, 2H), 7.39 – 7.34 (m, 1H), 7.31 – 7.26 (m, 3H), 2.72 – 2.64(m, 5H), 2.64 – 2.49 (m, 4H), 2.30 (td, J = 13.8, 3.8 Hz, 2H). 13 C NMR (151MHz, CDCl3) δ 161.36, 161.17, 136.70, 135.84, 133.33, 132.94 (q, J = 34.5Hz), 132.90 (q, J = 34.4 Hz), 129.61 (q, J = 3.7 Hz), 129.21, 129.09, 128.73,127.68 – 127.38 (m), 126.98, 124.98, 122.74 (q, J = 273.1 Hz), 122.70 (q, J =273.1 Hz), 121.00, 111.57, 41.22, 31.67, 27.66, 21.30. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 12F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 21 F 12 NO6, [M+Na]+ Calculated value: 766.1069, Measured value: 766.1069.

[0173] Step 2: Synthesis of Compound 9 (tellurium heterocyclic product) To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, add the purified bisperoxide S2 (0.1 mmol, 1.0 equivalent) prepared above. Transfer the flask to a nitrogen glove box, add 1,4-dioxane (0.8 mL), followed by trimethylchlorosilane (TMSCl, 0.7 mmol, 76.1 mg, 7.0 equivalent) and 0.1 M ferric chloride (FeCl3) dioxane solution (0.02 mmol, 0.2 mL, 20 mol%). Seal the reaction flask and remove it from the glove box, stirring at 25 °C for 24 hours (600 rpm). After removing the solvent by rotary evaporation under reduced pressure, the reaction flask was returned to a nitrogen glove box, and sodium telluride (Na₂Te, 0.5 mmol, 86.7 mg, 5.0 equivalence), DMF (0.8 mL), and deoxygenated water (0.8 mL) were added sequentially. The reaction flask was sealed and removed, placed on a preheated aluminum heating block, and stirred at 80 °C for 24 hours (600 rpm). After the reaction was complete, the mixture was cooled to room temperature, diluted with water (5 mL), and extracted with diethyl ether (4 × 2.5 mL). The organic extracts were combined, dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give target product 9 as a white solid (15.7 mg, 50% yield). The overall yield of the two steps from ketone 4 was 43%. Characterization data: R f = 0.4 (9% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.32 – 7.27 (m, 1H), 7.27 – 7.19 (m, 3H), 3.69(t, J = 12.8 Hz, 2H), 2.71 – 2.65 (m, 2H), 2.63 (s, 3H), 2.60 – 2.52 (m, 2H), 2.40 (t, J = 13.4 Hz, 2H). 13 C10 NMR (151 MHz, CDCl3) δ 138.77, 135.97, 133.15, 128.04, 126.72, 124.98, 120.47, 44.13, 38.30, 21.51, -7.02. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H 15 NTe, [M+H]+ Calculated value: 316.0339, measured value: 316.0338.

[0174] Example 8 Synthesis of Compound 11

[0175] Step 1: Synthesis of Diperoxide S3 Ketone 10 (3 mmol), 1,4-dioxane (3.0 mL), and ~60 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 28 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the target product, bisperoxide S3, as a white solid (2.16 g, 89% yield). Characterization data: 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 2H), 8.34 (s, 2H), 8.14 (s, 1H), 8.12 (s, 1H), 7.72 (d, J = 8.3 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 3.27 (dd, J = 10.1, 2.5 Hz, 2H), 3.10 (dd, J = 10.0, 7.1 Hz, 2H), 3.03 – 2.87 (m, 2H), 2.63 (dd, J = 14.8, 8.0 Hz, 2H), 2.40 (s, 3H), 2.23 (dd, J = 14.5, 6.2 Hz, 2H). 13 C NMR (101 MHz, CDCl3) δ 161.42, 160.99, 144.11, 132.86 (q, J = 34.4Hz), 132.17, 129.86, 129.77 – 129.35 (m), 129.13, 129.08, 128.14, 127.61 –127.33 (m), 122.71 (q, J = 273.6 Hz), 122.54, 53.54, 40.55, 38.11, 21.62. 19 FNMR (565 MHz, CDCl3) δ -63.01 (s, 6F), -63.02 (s, 6F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 23 F 12 NO8S, [M+H]+ Calculated value: 810.1026, Measured value: 810.1026.

[0176] Step 2: Synthesis of Compound 11 (Thioheterocyclic Product) To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, add the purified bisperoxide S3 (0.2 mmol, 1.0 equivalence) prepared above. Transfer the flask to a nitrogen glove box, add 1,4-dioxane (1.6 mL), followed by trimethylchlorosilane (TMSCl, 1.4 mmol, 152.1 mg, 7.0 equivalence) and 0.1 M ferric chloride (FeCl3) dioxane solution (0.04 mmol, 0.4 mL, 20 mol%). Seal the flask and remove it from the glove box, stirring at 25 °C for 24 hours (600 rpm). After removing the solvent by rotary evaporation under reduced pressure, the reaction flask was returned to a nitrogen glove box, and sodium sulfide (Na₂S, 1.0 mmol, 78 mg, 5.0 equivalence), DMF (1.6 mL), and deoxygenated water (0.8 mL) were added sequentially. The reaction flask was sealed and removed, placed on a preheated aluminum heating block, and stirred at 80 °C for 24 hours (600 rpm). After the reaction was complete, the mixture was cooled to room temperature, diluted with water (10 mL), and extracted with diethyl ether (4 × 5 mL). The organic extracts were combined, dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the target diheterocyclic compound 11 as a white solid (42.6 mg, 75% yield). The overall yield from ketone 10 was 67%. Characterization data: R f = 0.4 (petroleum ether / ethyl acetate / DCM = 10:1:4). 1 H NMR (600 MHz, CDCl3) δ 7.69 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 3.51 (dd, J = 9.4, 6.4 Hz, 2H), 2.94 – 2.84 (m, 6H), 2.46 (dd, J = 11.5, 3.0 Hz, 2H), 2.43 (s, 3H). 13 C10 NMR (151 MHz, CDCl3) δ 143.83, 132.97, 129.83, 127.85, 52.70, 47.21, 36.15, 21.69. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H 17 NO2S2, [M+H]+ Calculated value: 284.0773, Measured value: 284.0772.

[0177] Example 9 Synthesis of Compound 12

[0178] Step 1: Synthesis of Diperoxide S3 Ketone 10 (3 mmol), 1,4-dioxane (3.0 mL), and ~60 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 28 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the target product, bisperoxide S3, as a white solid (2.16 g, 89% yield). Characterization data: 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 2H), 8.34 (s, 2H), 8.14 (s, 1H), 8.12 (s, 1H), 7.72 (d, J = 8.3 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 3.27 (dd, J = 10.1, 2.5 Hz, 2H), 3.10 (dd, J = 10.0, 7.1 Hz, 2H), 3.03 – 2.87 (m, 2H), 2.63 (dd, J = 14.8, 8.0 Hz, 2H), 2.40 (s, 3H), 2.23 (dd, J = 14.5, 6.2 Hz, 2H). 13 C NMR (101 MHz, CDCl3) δ 161.42, 160.99, 144.11, 132.86 (q, J = 34.4Hz), 132.17, 129.86, 129.77 – 129.35 (m), 129.13, 129.08, 128.14, 127.61 –127.33 (m), 122.71 (q, J = 273.6 Hz), 122.54, 53.54, 40.55, 38.11, 21.62. 19 FNMR (565 MHz, CDCl3) δ -63.01 (s, 6F), -63.02 (s, 6F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 32 H 23 F 12 NO8S, [M+H]+ Calculated value: 810.1026, Measured value: 810.1026.

[0179] Step 2: Synthesis of Compound 12 (Selenium Heterocyclic Product) Purified bisperoxide S3 (0.2 mmol, 1.0 equivalence) was added to an 8 mL reaction flask equipped with a magnetic stir bar and dried in an oven. The flask was transferred to a nitrogen glove box, and 1,4-dioxane (1.6 mL) was added, followed by TMSCl (1.4 mmol, 152.1 mg, 7.0 equivalence) and 0.1 M FeCl3 dioxane solution (0.04 mmol, 0.4 mL, 20 mol%). The flask was sealed and removed, and stirred at 25 °C for 24 hours (600 rpm). After removing the solvent under reduced pressure, the flask was returned to the nitrogen glove box, and DMF (1.6 mL) and an in-situ prepared aqueous solution of sodium hydride hydride (NaHSe) (prepared from Se powder and NaBH4) were added. The reaction flask was sealed and removed, and stirred at 80 °C for 24 hours (600 rpm). After the reaction was complete, the mixture was cooled to room temperature, diluted with water (10 mL), and extracted with diethyl ether (4 × 5 mL). The organic extracts were combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give product 12, a biheterocyclic product containing sulfur and selenium atoms, as a white solid (47.9 mg, 72% yield). The overall yield from ketone 10 was 64%. Characterization data: R f = 0.4 (petroleum ether / ethyl acetate / DCM = 10:1:4). 1 H NMR (600 MHz, CDCl3) δ 7.70 (d, J = 8.4 Hz, 2H), 7.32 (d, J = 8.2 Hz, 2H), 3.49 (dd, J = 10.0, 6.8 Hz, 2H), 3.02 (dd, J =10.1, 5.6 Hz, 2H), 2.97 (dd, J = 10.6, 6.7 Hz, 2H), 2.94 – 2.87 (m, 2H), 2.51 (dd, J = 10.6, 4.1 Hz, 2H), 2.42 (s, 3H). 13 C10 NMR (151 MHz, CDCl3) δ 143.72, 133.51, 129.82, 127.55, 52.00, 49.31, 26.57, 21.65. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 13 H 17 NO2SSe, [M+H]+ Calculated value: 332.0218, Measured value: 332.0210.

[0180] Example 10 Preparation of Compound 14

[0181] Step 1: Synthesis of Diperoxide S4 Ketone 13 (3 mmol), dioxane (2.0 mL), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 24 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the target product, bisperoxide S4, as a white solid (2.25 g, 93% yield). Characterization data: R f = 0.25 (petroleum ether / ethyl acetate = 6:1). 1 H NMR (400 MHz, CDCl3) δ 8.35 (s, 2H),8.34 (s, 2H), 8.14 (s, 1H), 8.12 (s, 1H), 7.43 – 7.36 (m, 4H), 7.36 – 7.30(m, 1H), 5.19 (s, 2H), 4.53 (d, J= 15.2 Hz, 2H), 2.54 – 2.37 (m, 3H), 2.38 –2.21 (m, 1H), 2.18 – 2.01 (m, 4H). 13 C NMR (151 MHz, CDCl3) δ 161.20, 161.10,153.53, 136.53, 132.90 (q, J = 34.3 Hz), 132.84 (q, J = 34.3 Hz), 129.66 –129.46 (m), 129.25, 128.75, 128.39, 128.21, 127.61 – 127.27 (m), 122.73 (q, J = 273.1 Hz), 122.71 (q, J = 273.6 Hz), 112.24, 67.44, 51.78, 36.09, 35.32, 28.30, 27.45. 19 F NMR (565 MHz, CDCl3) δ -63.04 (s, 6F), -63.05 (s, 6F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 33 H 23 F 12 NO8, [M+H]+ Calculated value: 790.1305, Measured value: 790.1297.

[0182] Step 2: Synthesis of Compound 14 (Thioheterocyclic Product) To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, add the purified bisperoxide S4 (0.2 mmol, 1.0 equivalence) prepared above. Transfer the flask to a nitrogen glove box, add 1,4-dioxane (1.6 mL), followed by trimethylchlorosilane (TMSCl, 1.4 mmol, 152.1 mg, 7.0 equivalence) and 0.1 M ferric chloride (FeCl3) dioxane solution (0.04 mmol, 0.4 mL, 20 mol%). Seal the flask and remove it from the glove box, stirring at 25 °C for 24 hours (600 rpm). After removing the solvent by rotary evaporation under reduced pressure, the reaction flask was returned to a nitrogen glove box, and sodium sulfide (Na₂S, 1.0 mmol, 78 mg, 5.0 equivalence), DMF (1.6 mL), and deoxygenated water (0.8 mL) were added sequentially. The reaction flask was sealed and removed, placed on a preheated aluminum heating block, and stirred at 80 °C for 24 hours (600 rpm). After the reaction was complete, the mixture was cooled to room temperature, diluted with water (10 mL), and extracted with diethyl ether (4 × 5 mL). The organic extracts were combined, dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give sulfur-containing bicyclic compound 14 as a colorless liquid (26.7 mg, 51% yield). The overall yield from ketone 13 was 48%. Characterization data: R f = 0.2 (9% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.40 – 7.29 (m, 5H), 5.16 (s, 2H), 4.57 – 4.43 (m, 2H), 3.23 (d, J = 12.9 Hz, 1H), 3.11 (d, J = 12.8 Hz, 1H), 2.16 – 2.10 (m, 2H), 2.06 (s, 4H). 13 C10 NMR (151 MHz, CDCl3) δ 153.22, 136.85, 128.65, 128.18, 128.06, 66.99, 54.18, 32.33, 29.05, 28.22, 0.12. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 14 H 17 NO2S, [M+H]+ Calculated value: 264.1053, Measured value: 264.1051.

[0183] Example 11 Preparation of Compound 16

[0184] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S5 Ketone 15 (3 mmol), acetonitrile (12 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 14 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the target product, bisperoxide S5, as a white solid (1.85 g, 78% yield). Characterization data: Rf = 0.5 (petroleum ether / ethyl acetate = 10:1). 1 H NMR (400 MHz, CDCl3) δ 8.37 (s, 4H), 8.11 (s, 2H), 7.35 – 7.28 (m, 2H), 7.25 – 7.18 (m, 3H), 3.93 – 3.78 (m, 2H), 3.56 (dt, J = 13.3, 4.5Hz, 1H), 3.03 (t,J = 13.6 Hz, 1H), 2.77 (dd, J = 5.0, 3.8 Hz, 1H), 2.69 (dd, J = 14.6, 5.5 Hz, 1H), 2.59 – 2.48 (m, 1H), 2.45 (d, J = 13.4 Hz, 1H), 2.22(dd, J = 14.7, 3.5 Hz, 1H), 1.39 (d, J = 7.2 Hz, 3H), 0.93 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ 173.54, 161.39, 140.82, 132.84 (q, J = 34.2Hz), 132.79 (q, J = 34.6 Hz), 129.77 – 129.52 (m), 129.45, 129.30, 128.63,127.71, 127.47 – 127.28 (m), 127.40 – 127.06 (m), 122.77 (q, J = 272.9 Hz), 122.73 (q, J = 273.0 Hz), 114.62, 60.34, 51.93, 36.83, 32.82, 30.14, 29.88,20.92, 13.94. 19 F NMR (565 MHz, CDCl3) δ -63.03 (s, 6F), -63.07 (s, 6F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 34 H 26 F 12 O8, [M+NH4]+ Calculated value: 808.1774, Measured value: 808.1758.

[0185] Step 2: Synthesis of Compound 16 (Nitrogen Heterocyclic Product) To an 8 mL reaction flask equipped with a magnetic stir bar and oven-dried, add the purified bisperoxide S5 prepared above (0.2 mmol, 1.0 equivalence). Transfer the flask to a nitrogen glove box, add 1,4-dioxane (1.6 mL), followed by trimethylchlorosilane (TMSCl, 1.4 mmol, 152.1 mg, 7.0 equivalence) and 0.1 M ferric chloride (FeCl3) dioxane solution (0.04 mmol, 0.4 mL, 20 mol%). Seal the flask and remove it from the glove box, stirring at 25 °C for 24 hours (600 rpm). After removing the solvent by rotary evaporation under reduced pressure, potassium iodide (KI, 0.2 mmol, 33.2 mg, 1.0 equivalent) and potassium carbonate (K₂CO₃, 1.0 mmol, 138 mg, 5.0 equivalent) were added to the reaction flask outside the glove box. The reaction flask was then returned to the nitrogen glove box, and acetonitrile (0.8 mL) and N-Boc-1,3-diaminobicyclo[1.1.1]pentane (0.8 mmol, 4.0 equivalent) were added. The reaction flask was sealed and removed, placed on a preheated aluminum heating block, and stirred at 80 °C for 24 hours (600 rpm). After the reaction was complete, the mixture was cooled to room temperature, diluted with diethyl ether (4 mL), filtered through a short silica gel column, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the target product 16 as a colorless waxy substance (37.4 mg, yield 44%). The overall yield from ketone 15 was 34%. Characterization data: Rf = 0.3 (50% v / v ethyl acetate / n-hexane). 1 HNMR (600 MHz, CDCl3) δ 7.57 – 7.49 (m, 2H), 7.25 – 7.16 (m, 3H), 4.93 (s,1H), 3.90 – 3.80 (m, 2H), 3.27 (dd, J = 4.1 Hz, 4.1Hz 1H), 3.08 (dd, J =11.6, 3.5 Hz, 1H), 2.92 (dd, J = 11.3, 4.0 Hz, 1H), 2.46 (dd, J = 11.4, 4.0Hz, 1H), 2.35 (dd, J = 10.1, 5.5 Hz, 1H), 2.25 – 2.16 (m, 1H), 1.99 (s, 6H), 1.81 (t, J= 10.5 Hz, 1H), 1.45 (d, J = 6.2 Hz, 9H), 1.00 (t, J = 7.1 Hz, 3H), 0.93 (dd, J = 6.9, 2.0 Hz, 3H). 13 C10 NMR (151 MHz, CDCl3) δ 173.20, 142.15, 129.29, 128.55, 127.77, 126.59, 60.28, 59.85, 55.80, 54.88, 53.19, 52.71, 50.03, 43.84, 41.68, 28.42, 27.72, 18.23, 13.92. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 25 H 36 N2O4, [M+H]+ Calculated value: 429.2748, Measured value: 429.2741.

[0186] Example 12 Preparation of Compound 17

[0187] Step 1: Synthesis of bis[3,5-bis(trifluoromethyl)benzoylperoxy]ketal S5 Ketone 15 (3 mmol), acetonitrile (12 mL), SnCl2 (10 mol%, 57 mg), and 30 wt% H2O2 (9 mL) were added sequentially to a 100 mL flask. The reaction mixture was stirred at 40 °C for 14 hours, and the reaction progress was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with a 1:1 volume ratio of diethyl ether / ethyl acetate (Et2O / EtOAc, 60 mL). Deionized water (30 mL) was added, and the aqueous phase was extracted with a 1:1 Et2O / EtOAc mixture (3 × 60 mL). The organic layers were combined and washed with deionized water (30 mL). Subsequently, the washings were extracted again with a 1:1 Et2O / EtOAc mixture (60 mL). All organic layers were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was further concentrated under high vacuum using an oil pump for approximately 1 hour. The crude residue obtained from the post-treatment was transferred to a flask equipped with a magnetic stirrer and dissolved in EtOAc (30 mL). The solution was cooled to 0 °C, and 2,6-dimethylpyridine (3.0 equivalent, 9.0 mmol, 963 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (2.5 equivalent, 7.5 mmol, 2.07 g) were added sequentially. The reaction mixture was allowed to slowly and naturally rise to room temperature with stirring, and the reaction was monitored by TLC (the reaction was complete in approximately 2 hours). Subsequently, the mixture was washed with aqueous HCl solution (0.1 M, 60 mL), and the aqueous phase was extracted again with EtOAc (30 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the target product, bisperoxide S5, as a white solid (1.85 g, 78% yield). Characterization data: Rf = 0.5 (petroleum ether / ethyl acetate = 10:1). 1 H NMR (400 MHz, CDCl3) δ 8.37 (s, 4H), 8.11 (s, 2H), 7.35 – 7.28 (m, 2H), 7.25 – 7.18 (m, 3H), 3.93 – 3.78 (m, 2H), 3.56 (dt, J = 13.3, 4.5Hz, 1H), 3.03 (t, J = 13.6 Hz, 1H), 2.77 (dd, J = 5.0, 3.8 Hz, 1H), 2.69 (dd,J = 14.6, 5.5 Hz, 1H), 2.59 – 2.48 (m, 1H), 2.45 (d, J = 13.4 Hz, 1H), 2.22(dd, J = 14.7, 3.5 Hz, 1H), 1.39 (d, J = 7.2 Hz, 3H), 0.93 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ 173.54, 161.39, 140.82, 132.84 (q, J = 34.2Hz), 132.79 (q, J = 34.6 Hz), 129.77 – 129.52 (m), 129.45, 129.30, 128.63,127.71, 127.47 – 127.28 (m), 127.40 – 127.06 (m), 122.77 (q, J = 272.9 Hz), 122.73 (q, J = 273.0 Hz), 114.62, 60.34, 51.93, 36.83, 32.82, 30.14, 29.88,20.92, 13.94. 19 F NMR (565 MHz, CDCl3) δ -63.03 (s, 6F), -63.07 (s, 6F). High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C 34 H 26 F 12 O8, [M+NH4]+ Calculated value: 808.1774, Measured value: 808.1758.

[0188] Step 2: Synthesis of Compound 17 (Thioheterocyclic Product) Purified bisperoxide S5 (0.2 mmol, 1.0 equivalent) was added to an 8 mL reaction flask equipped with a magnetic stir bar and dried in an oven. The flask was transferred to a nitrogen glove box, and 1,4-dioxane (1.6 mL) was added, followed by TMSCl (1.4 mmol, 152.1 mg, 7.0 equivalent) and 0.1 M FeCl3 dioxane solution (0.04 mmol, 0.4 mL, 20 mol%). The flask was sealed and removed, and stirred at 25 °C for 24 hours (600 rpm). After removing the solvent by rotary evaporation under reduced pressure, the flask was returned to the nitrogen glove box, and sodium sulfide (Na2S, 1.0 mmol, 78 mg, 5.0 equivalent), DMF (1.6 mL), and deoxygenated water (0.8 mL) were added sequentially. The reaction flask was sealed and removed, then placed on a preheated aluminum heating block and stirred at 80 °C for 12 hours (600 rpm). (Note: The reaction time for this CS bond formation step was shortened from the conventional 24 hours to 12 hours). After the reaction was complete, the mixture was cooled to room temperature, diluted with water (10 mL), and extracted with diethyl ether (4 × 5 mL). The organic extracts were combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give sulfur-containing bicyclic compound 17 as a colorless liquid (29.4 mg, 55% yield). The overall yield from ketone 15 was 43%. Characterization data: Rf = 0.5 (5% v / v ethyl acetate / n-hexane). 1 H NMR (600 MHz, CDCl3) δ 7.29 – 7.24 (m,4H), 7.23 – 7.18 (m, 1H), 3.92 – 3.80 (m, 2H), 3.62 (dd, J = 13.1, 10.5 Hz,1H), 3.42 (ddd, J = 10.4, 4.7, 3.4 Hz, 1H), 3.32 (dd, J = 13.6, 3.5 Hz, 1H), 2.65 (t, J = 4.5 Hz, 1H), 2.60 (dd, J = 13.1, 3.5 Hz, 1H), 2.48 – 2.40 (m,1H), 2.26 (dd, J = 13.6, 4.9 Hz, 1H), 1.34 (d, J= 6.8 Hz, 3H), 0.96 (t, J =7.1 Hz, 3H). 13 C10 NMR (151 MHz, CDCl3) δ 173.51, 143.09, 128.22, 127.85, 126.71, 59.91, 52.26, 40.18, 30.69, 30.41, 28.44, 19.06, 13.91. High-resolution mass spectrometry (HRMS): Chemical formula ([M]): C10 15 H 20 O2S, [M+H]+ Calculated value: 265.1257, Measured value: 265.1253.

[0189] It should be understood that the above embodiments are exemplary and are not intended to encompass all possible implementations included in the claims. Various modifications and changes can be made to the above embodiments without departing from the scope of this disclosure. Similarly, the various technical features of the above embodiments can be arbitrarily combined to form other embodiments of the present invention that may not be explicitly described. Therefore, the above embodiments only illustrate several implementations of the present invention and do not limit the scope of protection of this patent.

Claims

1. A method for preparing the compound represented by formula (I), characterized in that, The method includes: S1: Compound a1 or a2 undergoes reaction 1 in the presence of Lewis acid and H2O2, and the product undergoes reaction 2 in the presence of base to give compound b; S2: Compound b undergoes reaction 3 in the presence of chloride and catalyst, and the product undergoes reaction 4 to give the compound shown in formula (I); ， Among them, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, halogen, alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxyl, nitro, and -OR. b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d Cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q1 groups; R1, R2 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally substituted by one or more Q2 groups; Or R4, R5 and the carbon atoms attached thereto form cycloalkyl or heterocyclic groups, wherein the cycloalkyl or heterocyclic groups are optionally replaced by one or more Q3 groups; R6 is selected from ; R7 is selected from alkyl and aryl groups; wherein the alkyl and aryl groups are optionally substituted with one or more Q4 groups; A is selected from O, S, Se, Te, N-R8 and C(R9)(R 10 ); R8 is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, cycloalkyl, heterocyclic, aryl, or heteroaryl group is optionally substituted by one or more Q5 groups; R9, R 10 Each of the following is independently selected from alkyl, alkoxy, alkenyl, alkynyl, cyano, hydroxy, nitro, cycloalkyl, heterocyclic, aryl, and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, or heteroaryl is optionally substituted by one or more Q6 groups; R' and R'' are each independently selected from alkyl groups, wherein the alkyl group is optionally replaced by one or more Q7 groups; Or R', R'' and the atoms attached thereto form a heterocyclic group, wherein the heterocyclic group is optionally replaced by one or more Q8; Q1, Q2, Q3, Q4, Q5, Q6, Q7, and Q8 are each independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano group, nitro group, hydroxyl group, amino group, carbonyl group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C6 alkenyl group, C2-C6 alkynyl group, and C6-C6 alkynyl group. 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, =NR a -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q Replaced; Each time it appears, R Q Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic groups, -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d and -SiR a 3, wherein the amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 The cycloalkyl group and the 3-12 membered heterocyclic group are each independently bound by one or more R groups. Q1 Replaced; Each time it appears, R Q1 Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 14 Aryl, 5-14 heteroaryl, C3-C 12 Cycloalkyl and 3-12 membered heterocyclic groups; Each time it appears, R a Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R b Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R c Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it appears, R d Selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 aryl and 5-14 heteroaryl groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylamino, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups are affected by one or more R x replace; Each time it occurs, the R x Each is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, 5-14 membered heteroaryl and C6-C 14 Aryl; n is 0, 1, 2, or 3.

2. The method as described in claim 1, characterized in that, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, and -OR. b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 heteroaryl groups, preferably from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, -OR b -OC(=O)R a -OC(=O)OR b -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -S(=O)2OR b -NR c R d -NR c S(=O)2R a -C(=O)OR b -C(=O)R a -C(=O)OR b -C(=O)NR c R d C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Or R1, R2 and the carbon atoms they are attached to form C3-C 12 Cycloalkyl groups, 3-12 membered heterocyclic groups, preferably C3-C8 cycloalkyl groups, 3-8 membered heterocyclic groups, wherein the 3-8 membered heterocyclic group contains 1-4 heteroatoms selected from N, O, and S; Or R4, R5 and the carbon atoms they are attached to form C3-C 12 Cycloalkyl groups, 3-12-membered heterocyclic groups, preferably C3-C8 cycloalkyl groups, 3-8-membered heterocyclic groups, wherein the 3-8-membered heterocyclic group contains 1-4 heteroatoms selected from N, O, and S.

3. The method according to any one of claims 1-2, characterized in that, R7 is selected from C1-C6 alkyl and C6-C6 alkyl groups. 14 Aryl group, preferably from C1-C4 alkyl and C6-C 10 Aryl; Preferably, R8 is selected from hydrogen, C1-C6 alkyl, C3-C6 alkyl, C4-C6 alkyl, C5-C6 alkyl, C6 ... 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 membered heteroaryl, preferably from hydrogen, C1-C4 alkyl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, R9, R 10 Each is independently selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, cyano, hydroxyl, nitro, C3-C 12 Cycloalkyl, 3-12 membered heterocyclic, C6-C 14 Aryl and 5-14 membered heteroaryl groups, preferably from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyano, hydroxyl, nitro, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, R' and R'' are each independently selected from C1-C6 alkyl groups, and more preferably from C1-C4 alkyl groups; Or R', R'' and the atoms attached to them form a heterocyclic group containing two O atoms, preferably a 5-8 membered heterocyclic group containing two O atoms.

4. The method according to any one of claims 1-3, characterized in that, Each time Q1, Q2, Q3, Q4, Q5, Q6, Q7, and Q8 appear, they are each independently selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b and -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time it occurs, R Q Each group is independently selected from hydrogen, deuterium, oxo group, thio group, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C6-C 10 Aryl, 5-10 membered heteroaryl, C3-C8 cycloalkyl, 3-8 membered heterocyclic, -OR b -OC(=O)R a -OS(=O)2R a -OP(O)R a 2. -OC(=O)OR b -OS(=O)2OR b -OS(=O)2NR c R d -OC(=O)NR c R d -OP(O)(OR) b )2、-OP(O)(OR b (NR) c R d ), -OP(O)(NR c R d )2、-SR b -S(=O)R a -S(=O)2R a -SC(=O)R a -S(=O)2OR b -S(O)(NR) c )R a -S(=O)2NR c R d -NR c R d -NR c S(=O)2R a -NR c S(=O)R a -NR c S(=O)2OR b -NR c S(=O)2NR c R d -NR c C(=O)NR c R d -NR c C(=O)R a -NR c C(=O)OR b -C(=O)OR b -C(=O)SR a -C(=S)R a -C(=O)R a -C(=O)OR b -C(=O)NR c R d The 3-8 membered heterocyclic group and the 5-10 membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time it occurs, R Q1 Each group is independently selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, carbonyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C6-C 10 Aryl, 5-10-membered heteroaryl, C3-C8 cycloalkyl and 3-8-membered heterocyclic groups, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O and S.

5. The method according to any one of claims 1-4, characterized in that, Each time it appears, R a Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time it occurs, R b Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time it occurs, R c Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time it occurs, R d Selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 alkylamino, C3-C8 cycloalkyl, 3-8 membered heterocyclic, C6-C 10 Aryl and 5-10-membered heteroaryl, wherein the 3-8-membered heterocyclic group and the 5-10-membered heteroaryl group contain 1-4 heteroatoms selected from N, O, and S; Preferably, each time R occurs, x Each is independently selected from hydrogen, deuterium, oxo, thio, halogen, cyano, nitro, hydroxyl, amino, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, 3-8 heterocyclic, 5-10 heteroaryl, and C6-C 10 Aryl groups, wherein the 3-8 membered heterocyclic groups and 5-10 membered heteroaryl groups contain 1-4 heteroatoms selected from N, O, and S.

6. The method according to any one of claims 1-5, characterized in that, In step S1, compound a1 or a2 undergoes reaction 1 in the presence of a Lewis acid and H2O2, and the product obtained after post-treatment reacts with... or Reaction 2 occurs, yielding compound b; Preferably, the Lewis acid is selected from one or more of tin tetrachloride, tin dichloride, silver trifluoromethanesulfonate, silver bis(trifluoromethanesulfonyl)imide, zinc chloride, zinc bromide, titanium tetrachloride, ferric chloride, lithium chloride, magnesium chloride, and aluminum chloride, with tin dichloride being the most preferred. Preferably, the alkali in step S1 is selected from organic or inorganic alkalis; Preferably, the organic base is selected from one or more of triethylamine, 2,6-dimethylpyridine, pyridine, N,N-diisopropylethylamine, n-butyllithium, diisopropylaminolithium, sodium acetate, potassium acetate, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicycloundec-7-ene, preferably from 2,6-dimethylpyridine. Preferably, the inorganic base is selected from one or more of potassium phosphate, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide.

7. The method according to any one of claims 1-6, characterized in that, In step S2, the chloride is selected from one or more of lithium chloride, sodium chloride, potassium chloride, magnesium chloride, calcium chloride, ferric chloride, ferrous chloride, cobalt chloride, nickel chloride, copper chloride, cuprous chloride, zinc chloride, TMSCl, TESCl, and TBSCl, preferably TMSCl; Preferably, the catalyst in step S2 is selected from one or more of iron salts, copper salts, ruthenium salts, nickel salts, and cobalt salts; more preferably from one or more of FeCl3, FeCl2, FeSO4, Fe2(SO4)3, Fe(OAc)2, Fe(OAc)3, Fe(acac)2, Fe(acac)3, Fe(ClO4)3, CuCl2, CuCl, RuCl3, RuCl4, NiCl2, and CoCl2, with FeCl3 being the most preferred. Preferably, when A is S, the reaction 4 is carried out in the presence of sulfide or hydrosulfide to obtain the product; Preferably, the sulfide or hydrosulfide is selected from one or more of sodium sulfide, potassium sulfide, lithium sulfide, lithium hydrosulfide, sodium hydrosulfide and potassium hydrosulfide, and is more preferably selected from sodium sulfide; Preferably, when A is Se, reaction 4 is a reaction that occurs in the presence of selenide or selenium hydride to obtain the product; Preferably, the selenide or selenide hydride is selected from one or more of sodium selenide, potassium selenide, lithium selenide, lithium selenide hydride, sodium selenide, potassium selenide and tetrabutylammonium hydroselenate, preferably sodium selenide; Preferably, the sodium selenide is obtained through in-situ preparation; Preferably, when A is Te, the reaction 4 is carried out in the presence of telluride or telluride hydride to obtain the product; Preferably, the telluride or telluride hydride is selected from one or more of sodium telluride, potassium telluride, lithium telluride, sodium telluride and potassium telluride, and is more preferably selected from sodium telluride.

8. The method according to any one of claims 1-7, characterized in that, When A is O, reaction 4 is a reaction with an aqueous solution of an inorganic base in the presence of a phase transfer catalyst to obtain the product; Preferably, the phase transfer catalyst is selected from one or more of tetramethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium bisulfate, tetrabutylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide, and triphenylmethylphosphonium chloride, and is more preferably a mixture of tetrabutylammonium iodide and tetrabutylammonium bisulfate; Preferably, the inorganic base is selected from one or more of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide, with sodium hydroxide being the most preferred.

9. The method according to any one of claims 1-8, characterized in that, When A is N-R8, reaction 4 is the product of reaction 3 reacting with H2N-R8 in the presence of iodide and base to obtain the product; Preferably, the iodide is selected from sodium iodide, potassium iodide, lithium iodide and tetrabutylammonium iodide, and more preferably from potassium iodide; Preferably, the alkali is selected from organic or inorganic alkalis; Preferably, the organic base is selected from one or more of triethylamine, 2,6-dimethylpyridine, pyridine, N,N-diisopropylethylamine, n-butyllithium, diisopropylaminolithium, sodium acetate, potassium acetate, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicycloundec-7-ene. Preferably, the inorganic base is selected from one or more of potassium phosphate, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, and potassium hydroxide, with potassium carbonate being the most preferred.

10. The method according to any one of claims 1-9, characterized in that, When A is C(R9)(R) 10 When ), reaction 4 is the product of reaction 3 reacting with CH2(R9)(R 10 The reaction proceeds to yield the product.

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