A dihydroisoxazole molecule and a method for synthesizing the same

Abstract

This invention discloses a dihydroisoxazole molecule, a method for synthesizing the compound, and its pharmaceutical applications. The quinoline group in the dihydroisoxazole molecule of this invention is of great significance for modifying molecules in the later stages of quinoline drug synthesis and for accelerating the screening of clinical drug candidates. The dihydroisoxazole molecule contains nitrogen and oxygen atoms with coordinating functions. As a ligand, the synthesized nitrogen-containing bicyclic compound can be used to design metal catalysts; as a molecular probe, the dihydroisoxazole molecule can be used for drug candidate discovery; and as a scaffold, the dihydroisoxazole molecule can be used in materials science.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis technology, specifically referring to a method for synthesizing quinoline-substituted isoxazole molecules. Background Technology

[0002] Quinolines and nitrogen-containing heterocycles such as isoxazoles are important structural units in bioactive natural products, drug molecules, and functional materials. Chemical modification of the quinoline core skeleton, especially in the later stages of drug synthesis, can accelerate the screening of clinical drug candidates. However, the relatively low reactivity of the quinoline group limits the efficiency of traditional methods for its introduction, hindering its further development in applied chemistry. Furthermore, the synthesis of quinoline derivatives primarily focuses on the attack of relatively stable alkyl radicals on quinoline ononium salts, such as secondary and tertiary alkyl radicals, while the coupling reaction between primary alkyl radicals and quinoline ononium salts remains a challenging task. Summary of the Invention

[0003] To address the aforementioned technical problems, the present invention aims to provide an effective method for synthesizing quinoline-substituted heterocyclic compounds with high selectivity, thereby overcoming the low reactivity of quinoline.

[0004] To achieve the above objectives, the present invention provides a compound of formula I, the structural formula of which is as follows:

[0005]

[0006] Among them, R 1 It is an aromatic group, alkyl group, or H, R 2 and R 3 It is an alkyl group or H, R 4 It is any one of alkyl, halogen, MeCO-, and H.

[0007] Preferably, R 1 It is phenyl, cycloalkyl, C1-6 straight-chain alkyl, alkylbenzene, furanyl, thiophene, or phenyl-R 5 Any one of them, R 2 and R 3 It is any one of C1-4 alkyl groups and H; R 4 It is any one of alkyl, MeCO-, halogen, and H.

[0008] Preferably, R 5 It is any one of MeO-, Cl, Br, NC-, phenyl, methane, or H.

[0009] Preferably, R 1 It is phenyl, cycloalkyl, propalkyl, hexyl, ethylphenyl, furanyl, thiophenyl, or phenyl-R5 Any one of them, R 2 and R 3 It is methyl or H; R 4 It is any one of methyl, MeCO-, halogen, and H.

[0010] Preferably, the compound of Formula I is selected from: 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-(p-tolyl)-4,5-dihydroisoxazole, 3-(4-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-([1,1'-biphenyl]-4-yl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(4-bromophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)- 4,5-Dihydroisoxazole, 3-(4-chlorophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4-(4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole-3-yl)benzonitrile, 3-(3-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(3-bromophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(3-chlorophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole Isoxazole, 3-(2-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-(naphthyl-2-yl)-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-(thiophen-2-yl)-4,5-dihydroisoxazole, 3-(furan-2-yl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole Isoxazole, 5-((4-methylquinoline-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 3-(4-methoxyphenyl)-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(4-chlorophenyl)-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 5-methyl-5-((4-methylquinoline-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-phenylethyl-4,5-dihydroisoxazole, 3-hexyl-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-propyl-4,5-dihydroisoxazole, 3-cyclohexyl-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole, 1-(2-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole-5-yl)methyl)quinolin-4-yl)ethane-1-one, 5-((4-bromoquinolin-2-yl)methyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole, 5-((4-chloroquinolin-2-yl)methyl)-4,4-dimethyl-3-phenyl 4,4-Dimethyl-5-((2-methylquinoline-4-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 4,4-dimethyl-3-phenyl-5-(quinoline-2-ylmethyl)-4,5-dihydroisoxazole, 4,4-dimethyl-3-phenyl-5-(quinoline-4-ylmethyl)-4,5-dihydroisoxazole, 5-(isoquinoline-1-ylmethyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole, or 5-(benzo[h]quinoline-4-ylmethyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole.

[0011] The present invention also provides a method for synthesizing the compound of Formula I, characterized in that the method includes the following steps: using oxime A and N-methoxyquinolineonium salt B as raw materials, the compound of Formula I is synthesized by visible light catalysis.

[0012] Preferably, the synthesis method is as follows:

[0013]

[0014] Preferably, oxime A, N-methoxyquinoline onion salt B, manganese acetate dihydrate, and a photocatalyst are mixed, and an organic solvent is added under an inert gas environment. The mixture is then irradiated with blue light and magnetically stirred until the reaction is complete. The resulting solution is extracted with ethyl acetate, and the combined organic phases are washed with saturated brine. The mixture is then dried with anhydrous sodium sulfate, concentrated under reduced pressure to dryness, and the concentrated crude product is purified by silica gel column chromatography to obtain compound I.

[0015] Preferably, the photocatalyst is bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate).

[0016] Preferably, the organic solvent includes any one of dichloromethane, acetonitrile, and 1,2-dichloroethane.

[0017] Preferably, the wavelength of the blue light is 440nm or 456nm, the light intensity is 10 watts, and the irradiation time is 10-16 hours.

[0018] The present invention also provides the use of compounds of Formula I in the preparation of pharmaceuticals for the treatment of liver cancer, breast cancer, or colon cancer.

[0019] Compared with the prior art, the technical solution of the present invention has the following innovative points:

[0020] The advantage of this invention is that it uses alkoxy radicals generated from N-methoxyquinoline onion salt under visible light catalysis as a further single-electron transfer initiator. At the same time, the electron-deficient quinoline onion salt can also act as a radical acceptor. The synthetic route is simple and economical.

[0021] Quinoline onium salts have high reactivity and the raw materials are easy to synthesize. Using quinoline onium salts as precursor molecules for introducing quinoline can effectively solve the problem of low reactivity of quinoline.

[0022] This invention provides a convenient, mild, and green synthetic method for constructing methylene-bridged bicyclic compounds, requiring only room temperature and light conditions for efficient reaction. The synthesized product contains a quinoline group, which is of great significance for molecular modification in the later stages of quinoline drug synthesis and for accelerating the screening of clinical drug candidates.

[0023] The synthesized quinoline-substituted heterocyclic molecules contain coordinating nitrogen and oxygen atoms. As ligands, the synthesized methylene-bridged nitrogen-containing bicyclic compounds can be used to design metal catalysts; as molecular probes, the synthesized methylene-bridged nitrogen-containing bicyclic compounds can be used for drug candidate discovery; and as scaffolds, the synthesized methylene-bridged bi-nitrogen-containing heterocyclic compounds can be used in materials science.

[0024] Activity tests showed that the synthesized nitrogen-containing bicyclic compounds exhibited varying degrees of anticancer activity against typical liver cancer cells (HepG2), breast cancer cells (MCF7), and colon cancer cell line (Caco2). Attached Figure Description

[0025] To make the technical problems solved by this invention, the technical means employed, and the technical effects achieved clearer, specific embodiments of this invention will be described in detail below with reference to the accompanying drawings. However, it should be noted that the drawings described below are merely drawings of exemplary embodiments of this invention. Those skilled in the art can obtain drawings of other embodiments based on these drawings without any creative effort.

[0026] Figure 1 This is a graph showing the relative cell viability trend of breast cancer cells (MCF7) corresponding to different concentrations of compound 3a in Example 12.

[0027] Figure 2 This is a graph showing the relative cell viability trends of liver cancer cells (HepG2) at different concentrations of compound 3a in Example 12.

[0028] Figure 3 This is a graph showing the relative cell viability trends of colon cancer cell lines (Caco2) corresponding to different concentrations of compound 3a in Example 12. Detailed Implementation

[0029] Exemplary embodiments of the invention will now be described more fully with reference to the accompanying drawings. While these exemplary embodiments can be implemented in various specific ways, they should not be construed as limiting the invention to the embodiments set forth herein. Rather, these exemplary embodiments are provided to make the content of the invention more complete and to facilitate a full communication of the inventive concept to those skilled in the art. Structures, performance, effects, or other features described in a particular embodiment, while consistent with the inventive concept, may be combined in any suitable manner with one or more other embodiments.

[0030] In the description of specific embodiments, detailed descriptions of structures, performance, effects, or other features are provided to enable those skilled in the art to fully understand the embodiments. However, this does not preclude those skilled in the art from implementing the present invention with technical solutions that do not contain the aforementioned structures, performance, effects, or other features under specific circumstances.

[0031] The flowcharts in the accompanying drawings are merely illustrative examples and do not imply that the solution of this invention must include all the content, operations, and steps shown in the flowcharts, nor do they imply that the execution must be performed in the order shown in the diagrams. For example, some operations / steps in the flowcharts can be decomposed, some operations / steps can be combined or partially combined, etc. Without departing from the inventive spirit of this invention, the execution order shown in the flowcharts can be changed according to the actual situation.

[0032] The box in the attached diagram Figure 1 Generally, these refer to functional entities, and do not necessarily correspond to physically independent entities. That is, these functional entities can be implemented in software, in one or more hardware modules or integrated circuits, or in different network and / or processing unit devices and / or microcontroller devices.

[0033] The same reference numerals in the accompanying drawings denote the same or similar elements, components, or parts, and therefore, repeated descriptions of the same or similar elements, components, or parts may be omitted below. It should also be understood that although terms such as first, second, third, etc., indicating numbers may be used herein to describe various devices, elements, components, or parts, these devices, elements, components, or parts should not be limited by these terms. That is, these terms are only used to distinguish one from another. For example, a first device may also be referred to as a second device, without departing from the essential technical solution of the invention. Furthermore, the terms "and / or" and "and / or" refer to all combinations including any one or more of the listed items.

[0034] This invention utilizes the methoxy radical to extract active hydrogen from oxime molecules, achieving highly selective synthesis of quinoline-substituted heterocyclic compounds. Using a nitrogen-methoxyquinoline onium salt as the reactant, under visible light catalysis, the NO bond in the quinoline onium salt breaks, and the resulting methoxy radical serves as the motive force for extracting active hydrogen, thereby designing and synthesizing substituted quinoline derivatives. Oxime molecules contain nucleophilic nitrogen / oxygen atoms, making them popular precursors for synthesizing nitrogen- or oxygen-containing heterocyclic compounds. The hydroxyl hydrogen in oxime molecules can be converted into oxygen radical intermediates by other heteroatom radicals via hydrogen extraction. Therefore, this invention reports a photochemical reaction to construct substituted quinoline derivatives and to synthesize diverse methylene-bridged dinitrogenous heterocyclic compounds.

[0035] Example 1

[0036] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction, the mixture was extracted with ethyl acetate (3 × 25 mL), and the combined organic phases were washed with saturated brine (1 × 30 mL). The mixture was then dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether:ethyl acetate = 3:1) to give 29.4 mg of methylene-bridged bicyclic compound 3a in solid form, with a yield of 89%. The reaction equation is as follows:

[0037]

[0038] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole (3a). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v petroleum ether / ethyl acetate, Rf = 0.4 in 3:1 v / v petroleum ether / ethyl acetate) gave a yellow solid, compound 3a (29.4 mg, 89%). mp = 110.5–111.0 °C. 1 HNMR(300MHz, CDCl3)δ8.06(dd,J=8.4,0.7Hz,1H),7.99(dd,J=8.3,1.0Hz,1H),7.72–7.65(m,3H),7.54(ddd,J=8.3,6.9,1.3Hz,1H ),7.42(dd,J=5.2,1.8Hz,4H),4.71(dd,J=9.6,3.8Hz,1H),3.29(ddd,J=17.9,14.1,6.7Hz,2H),2.72(s,3H),1.42(d,J=3.9Hz,6H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ165.2,158.4,147.7,144.6,129.6,129.5,129.3,129.1,128.6 ,127.4,127.1,125.8,123.7,123.0,90.0,51.5,37.9,24.1,19.8,18.7;IR(ATR)νmax 3061,2965,2927,1603,1562,1509,1464,1445,761cm –1 HRMS(ESI)Calcd for C 22 H 23 N₂O:[M+H] + =331.1805.Found:331.1797.

[0039] Example 2

[0040] In a 250 mL two-necked flask, oxime 1a (1.0 g, 1.0 equiv.), N-methoxyquinonium salt 2a (3.45 g, 2.5 equiv.), manganese acetate dihydrate (1.7 g, 1.2 equiv.), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (106 mg, 2 mol%) were added. The reaction system was protected with nitrogen and 50 mL of dichloromethane was added as the organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 50 mL). The combined organic phases were washed with saturated brine (1 × 50 mL), dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 3:1) to give 1.24 g of methylene-bridged bicyclic compound 3a, with a yield of 71%.

[0041] Example 3

[0042] In a 10 mL reaction tube, oxime A (20.3 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3b (21.3 mg), with an overall yield of 62%.

[0043] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-(p-tolyl)-4,5-dihydroisoxazole (3b). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in), gave compound 3b (21.3 mg, 62%) as a white solid, mp = 116.1–116.9 °C. 1H NMR (500MHz, CDCl3) δ8.90(d,J=8.5Hz,1H),8.17(d,J=8.4Hz,1H),7.99(dd, J=14.1,6.8Hz,1H),7.85–7.82(m,1H),7.79(d,J=6.2Hz,1H),7.56(d,J=8.1H z,2H),7.23(d,J=8.0Hz,2H),4.73(d,J=10.7Hz,1H),4.29(d,J=13.3Hz,1H) ,3.27(t,J=11.9Hz,1H),2.95(s,3H),2.39(s,3H),1.61(s,3H),1.47(s,3H); 13 C{ 1 H}NMR (126MHz, CDCl3) δ165.7,156.5,156.0,140.5,138.1,134.1,129.6,129.5,127.5 ,127.3,125.9,124.7,124.5,122.4,89.1,52.8,33.5,24.7,21.5,20.2,19.9;IR(ATR)ν max 2922,2853,2588,1644,1606,1466,765cm –1 HRMS(ESI)Calcd for C 23 H 25 N₂O:[M+H] + =345.1961.Found:345.1946.

[0044] Example 4

[0045] In a 10 mL reaction tube, oxime A (21.9 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3c (30.6 mg), with an overall yield of 85%.

[0046] 3-(4-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3c). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in), gave a yellow solid, compound 3c (30.6 mg, 85%). mp = 127.3–127.8 °C. 1 H NMR (300MHz, CDCl3) δ8.12(d,J=8.4Hz,1H),7.98(d,J=8.4Hz,1H),7.73–7.68(m,1H),7.64–7.59(m,2H),7.57–7.52(m,1H),7.4 2(s,1H),6.94–6.89(m,2H),4.65(dd,J=7.4,5.8Hz,1H),3.82(s,3H),3.31(d,J=7.4Hz,2H),2.72(s,3H),1.41(d,J=9.0Hz,6H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ165.0,160.9,158.5,129.8,128.9,128.7,127.2,126.3,1 23.9,123.3,121.8,114.2,89.9,55.5,51.7,37.6,24.4,20.0,19.0;IR(ATR)νmax 2966,2923,1606,1513,1464,1254,761cm –1 HRMS(ESI)Calcd for C 23 H 25 N₂O₂:[M+H] + =361.1911.Found:361.1897.

[0047] Example 5

[0048] In a 10 mL reaction tube, oxime A (26.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain quinoline-substituted isoxazole molecules 3d (28.4 mg), with an overall yield of 70%.

[0049] 3-([1,1'-biphenyl]-4-yl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3d). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.5 in 3:1 v / v petroleum ether / ethyl acetate), gave a white solid, compound 3d (28.4 mg, 70%), mp = 115.2–115.9 °C. 1 H NMR (400MHz, CDCl3) δ8.15(d,J=8.4Hz,1H),8.00(d,J=8.3Hz,1H),7.74(dd,J=18.4,8.1Hz,3H),7.63(dd,J=10.1,8.3Hz,4H),7.56(t,J=7.6Hz,1H), 7.46(dd,J=9.6,5.5Hz,3H),7.37(t,J=7.2Hz,1H),4.73(dd,J=8.0,5.2Hz ,1H),3.36(dd,J=11.3,7.0Hz,2H),2.74(s,3H),1.49(s,3H),1.46(s,3H); 13 C{ 1 H}NMR(101MHz,CDCl3)δ165.1,158.3,142.6,140.3,129.8,129.0,128.4,127.9,127 .4,127.2,127.2,126.3,123.9,123.3,90.2,51.7,37.6,24.4,20.0,19.0;IR(ATR)ν max3060,2966,2925,1602,1465,885,764cm –1 HRMS(ESI)Calcd for C 28 H 27 N₂O:[M+H] + =407.2118.Found:407.2101.

[0050] Example 6

[0051] In a 10 mL reaction tube, oxime A (26.7 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3e (29.0 mg), with an overall yield of 71%.

[0052] 3-(4-bromophenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3e). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (2:1 v / v petroleum ether / ethyl acetate), Rf = 0.7 in, gave a white solid 3e (29.0 mg, 71%), mp = 106.6–107.1 °C. 1 HNMR (400MHz, CDCl3) δ8.07(d,J=6.7Hz,1H),7.87(d,J=6.7Hz,1H),7.67(t,J=6.1Hz,1H),7.54(t,J=6.1Hz,1H),7.48(s,4H),7.4 3(s,1H),5.23(dd,J=8.1,2.3Hz,1H),4.27(d,J=10.9Hz,1H),4.09(dd,J=11.1,8.2Hz,1H),3.67(s,3H),2.62(s,3H),2.57(s,3H); 13 C{ 1H}NMR(101MHz, CDCl3)δ147.1,141.6,121.0,120.0,118.6,118.1,117.2,117.0,114.9,114.7,114.2,87.5,56.8,44.7,34.9,31.4,30.8; IR(ATR)ν max 3063,2966,2924,2853,1643,1603,1465,885,760cm –1 HRMS(ESI)Calcd for C 22 H 22 BrN2O:[M+H] + =409.0910.Found:409.0901.

[0053] Example 7

[0054] In a 10 mL reaction tube, oxime A (22.3 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain quinoline-substituted isoxazole molecule 3f (31.7 mg), with an overall yield of 87%.

[0055] 3-(4-Chlorophenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3f). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.3 in), yielded a pale yellow oily compound 3f (31.7 mg, 87%). 1H NMR (400MHz, CDCl3) δ7.93(d,J=6.7Hz,1H),7.82(d,J=6.7Hz,1H),7.60(t,J=6.1Hz,1H),7.52(d,J=6.8Hz,2H),7.47(t ,J=6.1Hz,1H),7.36–7.33(m,3H),5.21(t,J=5.3Hz,1H),4.09(d,J=5.3Hz,2H),3.61(s,3H),2.57(s,3H),2.55(s,3H); 13 C{ 1 H}NMR(101MHz,CDCl3)δ146.9,141.9,132.9,132.0,124.1,119.2,118.6,118.4,118 .4,117.8,117.2,116.4,114.5,114.0,87.6,56.6,45.4,34.8,31.3,30.6;IR(ATR)ν max 3062,2968,2927,1601,1493,1465,1092,759cm –1 HRMS(ESI)Calcd for C 22 H 22 ClN2O:[M+H] + =365.1415.Found:365.1404.

[0056] Example 8

[0057] In a 10 mL reaction tube, oxime A (21.4 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 3 g (27.3 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 77%.

[0058] 4-(4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (3 g). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.3 in 3:1 v / v petroleum ether / ethyl acetate), yielded 3 g (27.3 mg, 77%) of a pale yellow oil. mp = 144.7–145.2 °C. 1 H NMR (500MHz, CDCl3) δ8.54(s,1H),8.10(d,J=8.3Hz,1H),7.87(t,J=7.6Hz,1H),7.79(d,J=8.5Hz,2H),7.71(dd,J=14.1,8.1Hz,3 H),7.58(s,1H),4.82(dd,J=10.5,2.3Hz,1H),3.88(s,1H),3.29(dd,J=13.8,10.6Hz,1H),2.86(s,3H),1.56(s,3H),1.45(s,3H); 13 C{ 1 H}NMR (126MHz, CDCl3) δ164.1,156.7,133.7,132.6,132.3,129.5,128.2,128.0, 127.3,124.3,123.9,118.4,113.6,90.3,51.8,35.1,24.4,19.9,19.7;IR(ATR)ν max 3066,2968,2924,2228,1644,1604,1467,764cm –1 HRMS(ESI)Calcd for C 23 H 22 N3O:[M+H] + =356.1757.Found:356.1742.

[0059] Example 9

[0060] In a 10 mL reaction tube, oxime A (21.9 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecules 3h (31.3 mg), with an overall yield of 87%.

[0061] 3-(3-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3h). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound (3h, 31.3 mg, 87%). 1 H NMR (400MHz, CDCl3) δ8.12(d,J=8.4Hz,1H),7.97(dd,J=8.3,0.8Hz,1H),7.70(dd d,J=8.3,6.9,1.3Hz,1H),7.54(ddd,J=8.2,6.9,1.1Hz,1H),7.41(s,1H),7.31(t ,J=8.1Hz,1H),7.22–7.21(m,2H),6.95(ddd,J=8.3,2.5,0.9Hz,1H),4.70–4.67( m,1H),3.80(s,3H),3.31(d,J=7.2Hz,2H),2.71(s,3H),1.43(s,3H),1.40(s,3H); 13 C{ 1 H}NMR (101MHz, CDCl3) δ165.2,159.6,158.2,130.6,129.7,129.7,128.6,127.1,126.2 ,123.8,123.2,119.7,115.7,112.8,90.1,55.4,51.6,37.5,24.3,19.9,19.0;IR(ATR)ν max2965,2922,1602,1465,1239,1023,760cm –1 HRMS(ESI)Calcd for C 23 H 25 N₂O₂:[M+H] + =361.1911.Found:361.1898.

[0062] Example 10

[0063] In a 10 mL reaction tube, oxime A (26.7 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain quinoline-substituted isoxazole molecule 3i (34.3 mg), with an overall yield of 84%.

[0064] 3-(3-bromophenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3i). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.5 in), yielded a pale yellow oily compound 3i (34.3 mg, 84%). 1 H NMR (400MHz, CDCl3) δ8.12(d,J=8.4Hz,1H),8.00(d,J=8.3Hz,1H),7.83(s,1H),7.72(t,J=7.6Hz,1H),7.57(dd,J=16.2,8.2Hz, 3H),7.40(s,1H),7.29(t,J=7.9Hz,1H),4.74(dd,J=7.8,5.5Hz,1H),3.33–3.29(m,2H),2.73(s,3H),1.44(s,3H),1.41(s,3H); 13 C{ 1H}NMR(101MHz,CDCl3)δ164.1,158.1,132.8,131.6,130.4,130.2,129.6,128.9,127 .2,126.2,125.9,123.8,123.2,122.8,90.4,51.5,37.6,24.3,19.9,18.9;IR(ATR)ν max 3063,2965,2927,1602,1561,1465,917,758cm –1 HRMS(ESI)Calcd for C 22 H 22 BrN2O:[M+H] + =409.0910.Found:409.0896.

[0065] Example 11

[0066] In a 10 mL reaction tube, oxime A (22.3 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3j (26.2 mg), with an overall yield of 72%.

[0067] 3-(3-chlorophenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3j). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.6 in), yielded a pale yellow oily compound 3j (26.2 mg, 72%). 1H NMR (400MHz, CDCl3) δ7.96(d,J=6.7Hz,1H),7.84(d,J=6.6Hz,1H),7.62(t,J=6.0Hz,1H),7.57(s,1H),7.50–7.46 (m,2H),7.37–7.29(m,3H),5.23(dd,J=7.2,3.3Hz,1H),4.15–4.06(m,2H),3.62(s,3H),2.59(s,3H),2.56(s,3H); 13 C{ 1 H}NMR (101MHz, CDCl3) δ146.8,141.8,132.7,132.3,123.2,120.4,119.4,119.3,118.3, 117.4,117.2,116.5,115.8,114.5,114.0,87.7,56.6,45.3,34.8,31.3,30.6;IR(ATR)ν max 3065,2969,2927,1602,1465,887,760cm –1 HRMS(ESI)Calcd for C 22 H 22 ClN2O:[M+H] + =365.1415.Found:365.1399.

[0068] Example 12

[0069] In a 10 mL reaction tube, oxime A (21.9 mg, 0.1 mmol), N-methoxyquinoline onion salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain quinoline-substituted isoxazole molecule 3k (33.5 mg), with an overall yield of 93%.

[0070] 3-(2-Methoxyphenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3k). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.3 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 3k (33.5 mg, 93%). 1 H NMR (400MHz, CDCl3) δ8.16(s,1H),7.88(s,1H),7.69(s,1H),7.56(s,1H),7.51(s,1H),7.37(s,1H),7.20(s,1H),7.03(dd,J=10.2,4.6H z,2H),5.26(d,J=7.9Hz,1H),4.50(d,J=2.4Hz,3H),4.35(d,J=9.8Hz,1H),4.16–4.10(m,1H),3.69(s,3H),2.46(dd,J=15.4,2.1Hz,6H); 13 C{ 1 H}NMR(101MHz,CDCl3)δ148.0,141.8,141.8,120.3,120.2,117.2,117.2,116.7,11 4.7,114.5,111.8,110.0,104.4,86.4,59.9,58.7,44.7,34.6,30.9,30.6;IR(ATR)ν max 3063,2963,2924,1602,1462,1247,1023,758cm –1 HRMS(ESI)Calcd for C 23 H 25 N₂O₂:[M+H] + =361.1911.Found:361.1894.

[0071] Example 13

[0072] In a 10 mL reaction tube, oxime A (24.9 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 31 (26.1 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 67%.

[0073] 3-(3,4-Dimethoxyphenyl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3l). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.3 in 2:1 v / v petroleum ether / ethyl acetate), gave a pale yellow oily compound 3l (26.1 mg, 67%). 1 HNMR (500MHz, CDCl3) δ7.95(d,J=8.5Hz,1H),7.81(d,J=8.3Hz,1H),7.55–7.52(m,1H),7.39–7.36(m,1H),7.15(t,J=2.8Hz,1H),7.06(dd,J=8. 4,0.7Hz,1H),6.71(dd,J=8.4,0.9Hz,1H),4.52(dd,J=8.8,4.4Hz,1H),3.74(s,6H),3.20–3.12(m,2H),2.55(s,3H),1.29(s,3H),1.26(s,3H); 13 C{ 1 H}NMR (126MHz, CDCl3) δ164.7,158.4,150.5,149.0,147.0,145.3,129.4,128.8,127.1,126.0,123 .7,123.1,122.0,119.8,110.6,110.5,90.0,55.9,55.9,51.4,37.6,24.4,20.0,18.8;IR(ATR)νmax 2932,1602,1513,1463,1254,1022,759cm –1HRMS(ESI)Calcd for C 24 H 27 N₂O₃:[M+H] + =391.2016.Found:391.2000.

[0074] Example 14

[0075] In a 10 mL reaction tube, oxime A (23.9 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3m (26.6 mg), with an overall yield of 70%.

[0076] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-(naphth-2-yl)-4,5-dihydroisoxazole (3m). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.3 in), yielded a pale yellow oily compound 3m (26.6 mg, 70%). 1 H NMR (400MHz, CDCl3) δ8.08(d,J=6.6Hz,1H),7.94(s,1H),7.87(d,J=6.7Hz,1H),7.76–7.70(m,4H),7.67(t,J=6.1Hz,1H),7.54(t,J=6.1Hz,1H ),7.48–7.46(m,3H),5.27(dd,J=8.1,2.2Hz,1H),4.29(d,J=10.9Hz,1H),4.13(dd,J=11.1,8.2Hz,1H),3.67(s,3H),2.71(s,3H),2.66(s,3H); 13 C{ 1H}NMR (101MHz, CDCl3) δ147.7,141.8,122.5,121.8,119.9,118.3,118.3,117.7,117.4,117.2,117 .2,117.0,116.9,116.9,116.8,115.3,114.6,114.3,87.5,57.0,44.9,35.1,31.5,30.8;IR(ATR)ν max 3058,2966,2925,1643,1603,1464,821,756cm –1 HRMS(ESI)Calcd for C 26 H 25 N₂O:[M+H] + =381.1961.Found:381.1950.

[0077] Example 15

[0078] In a 10 mL reaction tube, oxime A (19.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain quinoline-substituted isoxazole molecule 3n (25.2 mg), with an overall yield of 75%.

[0079] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-(thiophen-2-yl)-4,5-dihydroisoxazole (3n). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (2:1 v / v petroleum ether / ethyl acetate, Rf = 0.6 in), yielded a pale yellow oily compound 3n (25.2 mg, 75%). 1H NMR (400MHz, CDCl3) δ8.11(d,J=8.4Hz,1H),7.98(d,J=8.3Hz,1H),7.70(t,J=7.6Hz,1H),7.54(t,J=7.6Hz,1H),7.39(dd,J =15.6,5.4Hz,3H),7.08–7.06(m,1H),4.72(t,J=6.7Hz,1H),3.32(d,J=6.8Hz,2H),2.71(s,3H),1.49(s,3H),1.43(s,3H); 13 C{ 1 H}NMR(101MHz,CDCl3)δ160.9,158.2,131.2,129.7,128.8,127.8,127.5,127 .2,127.0,126.2,123.9,123.3,90.3,51.7,37.7,24.6,20.0,18.9;IR(ATR)ν max 3066,2969,2926,1602,1463,882,760,710cm –1 HRMS(ESI)Calcd for C 20 H 21 N2OS:[M+H] + =337.1369.Found:337.1358.

[0080] Example 16

[0081] In a 10 mL reaction tube, oxime A (17.9 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3o (23.1 mg), with an overall yield of 72%.

[0082] 3-(furan-2-yl)-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3o). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (2:1 v / v) petroleum ether / ethyl acetate (Rf = 0.6 in 2:1 v / v petroleum ether / ethyl acetate), gave a pale yellow oily compound 3o (23.1 mg, 72%). 1 H NMR(300MHz, CDCl3)δ8.06–7.96(m,2H),7.69(ddd,J=8.4,6.9,1.5Hz,1H),7.56–7.50(m,2H),7.37(s,1H),6.84(dd,J=3.5,0 .7Hz,1H),6.49(dd,J=3.5,1.8Hz,1H),4.70(dd,J=9.2,4.1Hz,1H),3.35–3.19(m,2H),2.70(s,3H),1.45(s,3H),1.41(s,3H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ158.5,157.7,147.7,144.9,144.9,144.0,129.4,129.4,127 .3,126.0,123.9,123.2,111.6,111.4,89.9,51.4,38.1,24.5,19.9,18.9;IR(ATR)ν max 2961,2924,1603,1562,1464,1005,879,756cm –1 HRMS(ESI)Calcd for C 20 H 21 N₂O₂:[M+H] + =321.1598.Found:321.1593.

[0083] Example 17

[0084] In a 10 mL reaction tube, oxime A (16.1 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3p (23.3 mg), with an overall yield of 77%.

[0085] 5-((4-methylquinolin-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole (3p). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.6 in), gave a pale yellow oily compound 3p (23.3 mg, 77%). mp = 96.0–96.7 °C. 1 H NMR(500MHz, CDCl3)δ7.95(d,J=8.4Hz,1H),7.86(dd,J=8.3,0.5Hz,1H),7.60–7.55(m,3H),7.43(ddd,J=8.1,7.0,1.0Hz,1H),7.29– 7.26(m,3H),7.17(d,J=2.6Hz,1H),5.20(dq,J=10.3,6.6Hz,1H),3.39–3.31(m,2H),3.17(ddd,J=12.9,7.5,6.4Hz,2H),2.59(s,3H); 13 C{ 1 H}NMR (126MHz, CDCl3) δ157.6,156.7,147.6,144.6,129.9,129.6,129.3,129. 1,128.6,127.0,126.6,125.8,123.6,123.0,80.7,43.8,39.8,18.6;IR(ATR)ν max 3060,2921,1600,1446,1356,910,758,692cm –1 HRMS(ESI)Calcd for C 20 H19 N₂O:[M+H] + =303.1492.Found:303.1479.

[0086] Example 18

[0087] In a 10 mL reaction tube, oxime A (19.1 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3q (23.3 mg), with an overall yield of 70%.

[0088] 3-(4-Methoxyphenyl)-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3q). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.2 in 3:1 v / v petroleum ether / ethyl acetate), gave a pale yellow oily compound 3q (23.3 mg, 70%). mp = 109.8–110.4 °C. 1 H NMR (500MHz, CDCl3) δ8.16(d,J=8.5Hz,1H),7.98(dd,J=8.4,0.9Hz,1H),7.72(t,J=7.2Hz,1H),7.59–7.54(m,3H),7.34(s,1H),6.90–6.87(m ,2H),5.26(dq,J=13.5,6.9Hz,1H),3.81(s,3H),3.49–3.41(m,2H),3.36(dd,J=13.9,5.7Hz,1H),3.26(dd,J=16.6,7.3Hz,1H),2.71(s,3H); 13 C{ 1H}NMR(126MHz, CDCl3)δ161.1,157.5,156.6,130.0,128.3,127.2,126.5,123.9,123.5,122.2,114.2,80.4,55.4,43.2,40.4,19.0; IR(ATR)ν max 2926,2840,1605,1515,1357,1253,1178,762cm –1 HRMS(ESI)Calcd for C 21 H 21 N₂O₂:[M+H] + =333.1598.Found:333.1587.

[0089] Example 19

[0090] In a 10 mL reaction tube, oxime A (19.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3r (25.5 mg), with an overall yield of 76%.

[0091] 3-(4-Chlorophenyl)-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3r). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 3r (25.5 mg, 76%). mp = 125.3–125.9 °C. 1HNMR(400MHz, CDCl3) δ7.96(d,J=6.7Hz,1H),7.83(d,J=6.6Hz,1H),7.62(t,J=6.1Hz,1H),7.50 –7.49(m,3H),7.32–7.30(m,3H),5.70(td,J=11.0,5.3Hz,1H),4.24–4.04(m,4H),3.61(s,3H); 13 C{ 1 H}NMR(101MHz, CDCl3)δ141.2,140.3,132.5,124.3,119.4,118.6,118.2,117.8,117.1,116.6,114.6,114.1,80.2,50.0,47.3,30.6; IR(ATR)ν max 3062,2923,2852,1600,1494,1351,1092,829,761cm –1 HRMS(ESI)Calcd for C 20 H 18 ClN2O:[M+H] + =337.1102.Found:337.1086.

[0092] Example 20

[0093] In a 10 mL reaction tube, oxime A (17.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3S (23.4 mg), with an overall yield of 74%.

[0094] 5-Methyl-5-((4-methylquinolin-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole (3S). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.6 in), yielded colorless crystalline compound 3S (23.4 mg, 74%). mp = 174.7–175.2 °C. 1 H NMR (400MHz, CDCl3) δ8.01(d,J=6.7Hz,1H),7.83(d,J=6.7Hz,1H),7.62(t,J=6.1Hz,1H),7.51–7.50(m,3H),7.42(s,1H ),7.32–7.31(m,3H),4.38(d,J=13.5Hz,1H),4.23(q,J=10.8Hz,2H),3.94(d,J=13.5Hz,1H),3.63(s,3H),2.71(s,3H); 13 C{ 1 H}NMR(101MHz,CDCl3)δ141.2,141.2,119.5,119.4,119.3,118.4,117.8,11 7.2,116.8,116.7,114.9,114.6,85.3,53.1,51.3,36.6,30.7;IR(ATR)νmax 3061,2924,2852,1602,1446,1359,922,760,692cm –1 HRMS(ESI)Calcd for C 21 H 21 N₂O:[M+H] + =317.1648.Found:317.1642.

[0095] Example 21

[0096] In a 10 mL reaction tube, oxime A (21.7 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 3t (21.5 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 60%.

[0097] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-phenethyl-4,5-dihydroisoxazole (3t). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.7 in), gave a yellow oily compound 3t (21.5 mg, 60%). 1 H NMR (500MHz, CDCl3) δ8.00 (d, J=8.4Hz, 1H), 7.85 (dd, J=8.4, 0.9Hz, 1H), 7.57 (ddd, J=8.3,6.9,1.3Hz,1H),7.42(ddd,J=8.1,7.0,1.1Hz,1H),7.16(dd,J=10.2,4.6Hz, 2H),7.12–7.07(m,4H),4.38(dd,J=9.5,3.9Hz,1H),3.10(ddd,J=23.5,14.1,6.5Hz ,2H),2.89–2.86(m,2H),2.58(s,3H),2.40–2.37(m,2H),1.04(s,3H),1.01(s,3H); 13 C{ 1 H}NMR(126MHz, CDCl3)δ166.5,158.5,141.4,129.8,128.6,128.5,127.2,126.3,123.9,123.3,88.2,52.1,37.9,32.3,27.0,23.6,19.0; IR(ATR)ν max 3027,2964,2927,1603,1453,886,759,700cm –1HRMS(ESI)Calcd for C 24 H 27 N₂O:[M+H] + =359.2118.Found:359.2102.

[0098] Example 22

[0099] In a 10 mL reaction tube, oxime A (19.7 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 3 u (22.7 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 67%.

[0100] 3-Hexyl-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3u). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.8 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 3u (22.7 mg, 67%). 1 H NMR(300MHz, CDCl3)δ8.28(d,J=8.3Hz,1H),8.03–8.00(m,1H),7.79–7.73(m,1H), 7.61(dd,J=11.2,4.1Hz,1H),7.47(s,1H),4.48(dd,J=10.1,3.1Hz,1H),3.45(d,J =13.7Hz,1H),3.19(dd,J=13.9,10.1Hz,1H),2.75(s,3H),2.25–2.20(m,2H),1.69 –1.63(m,2H),1.38–1.27(m,6H),1.23(s,3H),1.18(s,3H),0.88(t,J=6.7Hz,3H); 13 C{ 1H}NMR (75MHz, CDCl3) δ167.3,158.1,130.9,127.2,127.1,126.8,124.1,123.7, 87.9,52.4,36.7,31.7,29.3,26.2,25.0,23.8,22.7,19.3,19.0,14.2;IR(ATR)ν max 2925,2855,1604,1466,1261,1021,799,761cm –1 HRMS(ESI)Calcd for C 22 H 31 N₂O:[M+H] + =339.2431.Found:339.2423.

[0101] Example 23

[0102] In a 10 mL reaction tube, oxime A (15.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 3v (18.7 mg), with an overall yield of 63%.

[0103] 4,4-Dimethyl-5-((4-methylquinolin-2-yl)methyl)-3-propyl-4,5-dihydroisoxazole (3v). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1v / v) petroleum ether / ethyl acetate (Rf = 0.8 in 2:1v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 3v (18.7 mg, 63%). 1H NMR (300MHz, CDCl3) δ8.02 (ddd, J=8.4, 1.3, 0.6Hz, 1H), 7.94 (dd, J=8.7, 1.2H z,1H),7.65(ddd,J=8.4,6.8,1.5Hz,1H),7.49(ddd,J=8.3,6.9,1.3Hz,1H),7 .34(s,1H),4.45(dd,J=9.3,4.1Hz,1H),3.25–3.09(m,2H),2.66(s,3H),2.21 –2.16(m,2H),1.75–1.62(m,2H),1.15(d,J=4.7Hz,6H),0.98(t,J=7.4Hz,3H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ166.8,158.8,147.6,144.7,129.2,129.2,127.1,125.8 ,123.8,123.1,88.1,51.9,38.4,27.0,23.6,19.6,19.0,18.8,14.1;IR(ATR)ν max 2963,2930,2872,1603,1562,1509,1466,885,759cm –1 HRMS(ESI)Calcd for C 19 H 25 N₂O:[M+H] + =297.1961.Found:297.1986.

[0104] Example 24

[0105] In a 10 mL reaction tube, oxime A (19.5 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 3w (20.5 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 61%.

[0106] 3-Cyclohexyl-4,4-dimethyl-5-((4-methylquinolin-2-yl)methyl)-4,5-dihydroisoxazole (3w). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.5 in 4:1 v / v petroleum ether / ethyl acetate), gave a yellow oily compound 3w (20.5 mg, 61%). 1 H NMR (300MHz, CDCl3) δ8.02 (dd, J=8.0, 1.1Hz, 1H), 7.94 (dd, J=8.3, 1.4Hz, 1H), 7.66 (ddd,J=8.4,6.8,1.5Hz,1H),7.49(ddd,J=8.2,6.8,1.3Hz,1H),7.35(s,1H),4.40( dd,J=9.2,4.1Hz,1H),3.24–3.08(m,2H),2.66(s,3H),2.15(tt,J=11.7,3.3Hz,1H) ,1.87–1.77(m,4H),1.68–1.41(m,3H),1.30–1.24(m,3H),1.18(s,3H),1.15(s,3H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ170.8,158.9,147.5,144.7,129.2,127.1,125.8,123.8,1 23.2,88.1,52.4,38.3,35.7,32.4,32.2,26.5,25.8,23.7,19.2,18.8;IR(ATR)ν max 2926,2852,1602,1561,1509,1447,892,757cm –1 HRMS(ESI)Calcd for C 22 H 29 N₂O:[M+H] + =337.2274.Found:337.2433.

[0107] Example 25

[0108] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (72.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 4a (21.5 mg), with an overall yield of 60%.

[0109] 1-(2-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl)quinolin-4-yl)ethane-1-one (4a). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.6 in 2.5:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 4a (21.5 mg, 60%). 1 H NMR(500MHz, CDCl3)δ8.43(dd,JJ=8.5,0.9Hz,1H),8.09(dd,J=8.4,0.5Hz,1H),7.77(s,1H),7.75–7.72(m,1H),7.67–7.65(m,2H),7.61–7.58(m,1H) ,7.43–7.39(m,3H),4.70(dd,J=10.0,3.3Hz,1H),3.41(dd,J=14.2,10.0Hz ,1H),3.32(dd,J=14.2,3.3Hz,1H),2.78(s,3H),1.46(s,3H),1.42(s,3H); 13 C{ 1 H}NMR(126MHz, CDCl3)δ210.9,201.5,165.3,158.5,148.8,143.0,129.9,129.8,129.3,129.3, 128.6,127.7,127.4,125.4,122.5,121.3,111.5,89.8,51.6,38.1,30.1,24.2,19.8;IR(ATR)ν max3062,2967,2921,1692,1592,1463,891,766,696cm –1 HRMS(ESI)Calcd for C 23 H 23 N₂O₂:[M+H] + =359.1754.Found:359.1738.

[0110] Example 26

[0111] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (81.2 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 4b (24.0 mg), with an overall yield of 61%.

[0112] 5-((4-bromoquinoline-2-yl)methyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole (4b). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.7 in 2:1 v / v petroleum ether / ethyl acetate), yielded a yellow oily compound 4b (24.0 mg, 61%). 1 H NMR(500MHz, CDCl3)δ8.16(dd,J=8.3,0.8Hz,1H),8.07(d,J=8.4Hz,1H),7.87(s,1H),7.75–7.72(m,1H),7.66–7.64(m,2H) ,7.61–7.58(m,1H),7.42–7.38(m,3H),4.70(dd,J=9.3,4.0Hz,1H),3.30(qd,J=14.2,6.7Hz,2H),1.43(s,3H),1.39(s,3H); 13 C{ 1H}NMR (126MHz, CDCl3) δ165.1,158.6,147.9,134.7,130.5,129.7,129.2,128.9, 128.6,127.4,127.3,126.6,126.6,126.2,89.6,51.5,37.4,24.2,19.7;IR(ATR)ν max 3061,2968,1584,1553,1492,908,762,694cm –1 HRMS(ESI)Calcd for C 21 H 20 BrN2O:[M+H] + =395.0754.Found:395.0740.

[0113] Example 27

[0114] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (70.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 4c (22.4 mg), with an overall yield of 64%.

[0115] 5-((4-chloroquinoline-2-yl)methyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole (4c). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.5 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 4c (22.4 mg, 64%). 1H NMR(400MHz, CDCl3)δ8.23(dd,J=8.4,0.9Hz,1H),8.15(d,J=8.4Hz,1H),7.81–7.77(m,1H),7.70(s,1H),7.6 7–7.62(m,3H),7.44–7.40(m,3H),4.70(dd,J=8.6,4.7Hz,1H),3.38–3.29(m,2H),1.46(s,3H),1.41(s,3H); 13 C{ 1 H}NMR (101MHz, CDCl3) δ165.4,158.7,147.7,144.0,131.1,129.9,129.8,129.3, 128.8,128.5,127.5,125.5,124.3,122.7,89.7,51.8,37.5,24.4,19.9;IR(ATR)ν max 3062,2966,2926,1588,1494,917,763,695cm –1 HRMS(ESI)Calcd for C 21 H 20 ClN2O:[M+H] + =351.1259.Found:351.1244.

[0116] Example 28

[0117] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (65.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecules 4d (26.4 mg), with an overall yield of 80%.

[0118] 4,4-Dimethyl-5-((2-methylquinolin-4-yl)methyl)-3-phenyl-4,5-dihydroisoxazole (4d). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in 3:1 v / v petroleum ether / ethyl acetate), gave a yellow solid, compound 4d (26.4 mg, 80%). mp = 117.9–118.6 °C. 1 HNMR(300MHz, CDCl3)δ8.09(d,J=8.4Hz,1H),7.99(d,J=9.2Hz,1H),7.73–7.66(m,3H),7.57–7.51(m,1H ),7.45–7.41(m,4H),4.52(dd,J=9.2,3.7Hz,1H),3.45–3.31(m,2H),2.77(s,3H),1.47(d,J=2.8Hz,6H); 13 C{ 1 H}NMR (75MHz, CDCl3) δ165.3,158.7,147.9,143.8,129.9,129.5,129.2,129.2,128.7 ,127.3,125.8,125.7,123.0,122.8,89.4,51.6,30.4,25.2,24.0,19.7;IR(ATR)νmax 3061,2920,2850,1648,1603,1467,902,766,695cm –1 HRMS(ESI)Calcd for C 22 H 23 N₂O:[M+H] + =331.1805.Found:331.1798.

[0119] Example 29

[0120] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (61.8 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 3:1) to give quinoline-substituted isoxazole molecule 4e (23.7 mg) (C6:C4 = 1.2:1), with an overall yield of 75%.

[0121] 4,4-Dimethyl-3-phenyl-5-(quinolin-2-ylmethyl)-4,5-dihydroisoxazole (4e-C6) (C6:C4 = 1.2:1). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.5 in 3:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 4e-C6 (13.0 mg, 41%). 1 H NMR (500MHz, CDCl3) δ8.15(d,J=8.4Hz,1H),8.09(d,J=8.5Hz,1H),7.81(d,J=8.1Hz,1H),7.71(ddd,J=8.4,6.9,1.4Hz,1H),7.67–7.64(m,2H), 7.53(ddd,J=10.0,8.0,4.7Hz,2H),7.42–7.38(m,3H),4.72(dd,J=9.4,4.0Hz,1H),3.36(ddd,J=18.0,14.1,6.7Hz,2H),1.41(d,J=4.1Hz,6H); 13 C{ 1 H}NMR(126MHz, CDCl3)δ165.2,158.7,136.8,129.6,129.4,128.5,128.5,127.6,127.4,127.0,126.2,122.4,89.9,51.5,37.8,24.2,19.8; IR(ATR)ν max 3058,2968,2927,1619,1599,1504,1464,901,767,696cm –1HRMS(ESI)Calcd for C 21 H 21 N₂O:[M+H] + =317.1648.Found:317.1643.

[0122] 4,4-Dimethyl-3-phenyl-5-(quinolin-4-ylmethyl)-4,5-dihydroisoxazole (4e-C4) (C6:C4 = 1.2:1). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (3:1 v / v) petroleum ether / ethyl acetate (Rf = 0.2 in 3:1 v / v petroleum ether / ethyl acetate), gave a yellow solid, 4e-C4 (10.7 mg, 34%). mp = 167.8–168.3 °C. 1 H NMR(500MHz, CDCl3)δ8.86(d,J=4.3Hz,1H),8.17(d,J=8.4Hz,1H),8.04(d,J=8.4Hz,1H),7.72(t,J=7.6Hz,1H),7.65–7.63(m,2H),δ7.5 9(t,J=7.8Hz,1H),7.48(d,J=4.4Hz,1H),7.42–7.38(m,3H),4.48(dd,J=6.8,6.1Hz,1H),3.39(d,J=6.7Hz,2H),1.43(d,J=10.3Hz,6H); 13 C{ 1 H}NMR (126MHz, CDCl3) δ165.2,149.7,147.8,144.3,130.0,129.8,129.3,129.1,128.6,12 8.5,127.4,127.4,127.3,126.7,123.1,122.0,89.4,51.5,30.4,23.9,19.6;IR(ATR)νmax 3061,2967,2926,1592,1509,1464,901,766,696cm –1 ;HRMS(ESI)Calcd for C21H21N2O:[M+H] + =317.1648.Found:317.1635.

[0123] Example 30

[0124] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (61.8 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) with magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give quinoline-substituted isoxazole molecule 4f (19.3 mg), with an overall yield of 61%.

[0125] 5-(isoquinoline-1-ylmethyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole (4f). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (2:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in 2:1 v / v petroleum ether / ethyl acetate), yielded a pale yellow oily compound 4f (19.3 mg, 61%). 1 H NMR (300MHz, CDCl3) δ=8.49(d,J=5.7,1H),8.28–8.25(m,1H),7.84(d,J=7.3,1H),7.73–7.64(m,4H),7.58(d,J=5.7,1H),7. 42–7.40(m,3H),4.84(dd,J=8.9,4.2,1H),3.89(dd,J=14.4,8.9,1H),3.44(dd,J=14.4,4.2,1H),1.47(s,3H),1.41(s,3H); 13 C{ 1 H}NMR(75MHz, CDCl3)δ165.6,158.3,136.8,131.0,129.9,129.6,128.8,128.0,127.6,127.5,126.1,120.7,90.3,51.8,33.5,24.3,20.0; IR(ATR)ν max 2923,2852,1624,1587,1464,1390,899,767,696cm –1 HRMS(ESI)Calcd for C 21 H 21 N₂O:[M+H] +=317.1648.Found:317.1670.

[0126] Example 31

[0127] In a 10 mL reaction tube, oxime A (18.9 mg, 0.1 mmol), N-methoxyquinonium salt B (74.3 mg, 0.25 mmol), manganese acetate dihydrate (32.2 mg, 0.12 mmol), and the photocatalyst bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate) salt (2.0 mg, 2 mol%) were added. The reaction solution was protected with nitrogen and 1 mL of dichloromethane was added as organic solvent. The reaction was carried out under blue light (wavelength 456 nm, light intensity 10 W) irradiation and magnetic stirring for 16 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 25 mL). The combined organic phases were washed with saturated brine (1 × 30 mL), dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to give 4 g (19.0 mg) of quinoline-substituted isoxazole molecules, with an overall yield of 52%.

[0128] 5-(benzo[h]quinoline-4-ylmethyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole (4 g). Subsequent standard post-treatment and rapid column chromatography on silica gel, eluting with (5:1 v / v) petroleum ether / ethyl acetate (Rf = 0.4 in 5:1 v / v petroleum ether / ethyl acetate), yielded 4 g (19.0 mg, 52%) of a pale yellow oil. 1 H NMR (300MHz, CDCl3) δ9.36 (dd, J=7.6, 1.3Hz, 1H), 8.95 (d, J=4.6Hz, 1H), 7.92–7.82 (m, 3H), 7.72 (ddd, J=9.1, 7.5, 1.5Hz, 2H), 7.68–7. 65(m,2H),7.56(d,J=4.6Hz,1H),7.42(dd,J=5.2,1.9Hz,3H),4.51(dd,J=8.2,4.7Hz,1H),3.44–3.39(m,2H),1.45(s,3H),1.41(s,3H); 13 C{ 1H}NMR (75MHz, CDCl3) δ165.4,148.4,146.6,143.8,133.2,131.9,129.9,129.3,128.7,128.3,1 27.9,127.8,127.4,127.3,125.3,124.9,123.1,120.6,89.8,51.6,30.8,24.1,19.8;IR(ATR)ν max 3053,2925,1621,1586,1443,905,830,727,693cm –1 HRMS(ESI)Calcd for C 25 H 23 N₂O:[M+H] + =367.1805.Found:367.1806.

[0129] The activities of the compounds obtained from the reactions in Examples 1-31 above are shown in Table 1.

[0130]

[0131]

[0132]

[0133]

[0134] Example 32

[0135] Compound 3a obtained in Example 1 was prepared in concentration gradients (0, 1, 5, 10, 50, and 200 μM). The effects of compound 3a on the viability of breast cancer cells (MCF7), liver cancer cells (HepG2), and colon cancer cell line (Caco2) were determined using the MTT assay. The cytotoxicity of these compounds was studied using the Cell Counting Kit-8 (CCK-8) assay. The specific steps were as follows: Tumor cells were seeded in 96-well plates (3000 cells / well) and cultured overnight, then incubated with the compounds at concentrations of 0, 1, 5, 10, 50, and 200 μM for 48 hours, respectively. Subsequently, 20 μL of CCK-8 solution (Beyotime, Shanghai, China) was added to each well and incubated for 4 hours. The absorbance of each sample was measured at 450 nm using a microplate reader (Tecan Infinite M1000Pro). The relative cell viability of each sample was normalized using DMSO control. The IC50 of the compounds on tumor cells was calculated based on cell viability. 50 Value. (Cell viability % = OD of sample treatment group) 570 / Mean OD of blank control group570 (x100%).

[0136] Depend on Figure 1-3 It can be seen that compound 3a has a significant inhibitory effect on the proliferation of MCF7, HepG2, and Caco2 cancer cells. After 48 hours of treatment, the IC50 of MCF7, HepG2, and Caco2 cells was significantly reduced. 50 The values ​​were 78.32±3.15μM, 38.71±0.75μM, and 39.5±3.31μM, respectively.

[0137] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0138] It should be noted that, for the sake of simplicity, the foregoing method embodiments are all described as a series of actions. However, those skilled in the art should understand that the present invention is not limited to the described order of actions, because according to the present invention, some steps can be performed in other orders or simultaneously. Furthermore, those skilled in the art should also understand that the embodiments described in the specification are preferred embodiments, and the actions and modules involved are not necessarily essential to the present invention.

[0139] In the above embodiments, the descriptions of each embodiment have different focuses. For parts not described in detail in a certain embodiment, please refer to the relevant descriptions in other embodiments.

[0140] The above embodiments are only used to illustrate the technical solutions of the present invention, and are not intended to limit it. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

[0141] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent application. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the protection scope of this application. Therefore, the protection scope of this patent application should be determined by the appended claims.

Claims

1. A compound, characterized in that, The structure is shown in Equation I below: The compound of Formula I is selected from the following compounds: 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-(p-tolyl)-4,5-dihydroisoxazole, 3-(4-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-([1,1'-biphenyl]-4-yl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(4-bromophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5- Dihydroisoxazole, 3-(4-chlorophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4-(4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole-3-yl)benzonitrile, 3-(3-methoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(3-bromophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(3-chlorophenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 3-(2- 3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-(thiophen-2-yl)-4,5-dihydroisoxazole, 3-(furan-2-yl)-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 5-((4-methylquinoline-2-yl)methyl)-3-phenyl-4,5-dihydroisoxazole, 3-(4-methoxyphenyl)- ... 2-(4-methyl)methyl)-4,5-dihydroisoxazole, 3-(4-chlorophenyl)-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-phenylethyl-4,5-dihydroisoxazole, 3-hexyl-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-3-propyl-4,5-dihydroisoxazole, 3-cyclohexyl-4,4-dimethyl-5-((4-methylquinoline-2-yl)methyl)-4,5-dihydroisoxazole, 1-(2-((4,4-dimethyl-3-phenyl-4,5-Dihydroisoxazole-5-yl)methyl)quinoline-4-yl)ethane-1-one, 5-((4-bromoquinoline-2-yl)methyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole, 5-((4-chloroquinoline-2-yl)methyl)-4,4-dimethyl-3-phenyl-4,5-dihydroisoxazole, 4,4-dimethyl-3-phenyl-5-(quinoline-2-ylmethyl)-4,5-dihydroisoxazole, or 4,4-dimethyl-3-phenyl-5-(quinoline-4-ylmethyl)-4,5-dihydroisoxazole.

2. The method for synthesizing the compound according to claim 1, characterized in that, The method includes the following steps: oxime A, N-methoxyquinoline onion salt B, manganese acetate dihydrate, and a photocatalyst are mixed. Under an inert gas environment, an organic solvent is added, and the mixture is irradiated with blue light and magnetically stirred until the reaction is complete. The reaction solution is extracted with ethyl acetate, and the combined organic phases are washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The concentrated crude product is purified by silica gel column chromatography to obtain compound I. The photocatalyst is bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bipyridine]iridium di(hexafluorophosphate), and the organic solvent is dichloromethane. The synthesis process is as follows: Wherein, the compound of formula I is defined as described in claim 1.

3. The method for synthesizing the compound according to claim 2, characterized in that, The blue light has a wavelength of 440nm or 456nm, a light intensity of 10 watts, and an irradiation time of 10-16 hours.

4. The use of the compound according to claim 1 in the preparation of a medicament for the treatment of liver cancer, breast cancer, or colon cancer.

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