An electrochemical synthesis method for constructing oxo-polyheterocyclic compounds

Abstract

The application provides an electrochemical synthesis method for constructing oxo multi-heterocyclic compounds, and relates to the technical field of preparation of oxo multi-heterocyclic compounds. The specific steps are as follows: alcohol compounds are added into an electrochemical reaction bottle, a halogen source and a solvent are added into the bottle, then an electrode is inserted and an electric current or voltage is applied, and the product is prepared after the reaction is sufficiently carried out. The application provides a method for constructing oxo multi-heterocyclic compounds through electrochemical intramolecular cyclization reaction, which mainly utilizes cheap metal halide salt, loses electrons under anodic oxidation condition, and reacts with olefins to obtain a three-membered ring halonium salt structure, nucleophilic addition ring opening and cyclization of the intramolecular hydroxyl structure and the structure obtain the target product, and different ring number products can be constructed by changing the chain length and heteroatom substitution of the substrate. The synthesis method has the advantages of no transition metal catalysis, various product structures, simple operation, simple steps, high atom utilization rate, relatively stable chemical properties, low cost, easy purification and the like.

Description

Technical Field

[0001] This invention relates to the technical field of preparing oxo-containing multi-component heterocyclic compounds, and specifically to an electrochemical synthesis method for constructing oxo-containing multi-component heterocyclic compounds. Background Technology

[0002] Tetrahydrofurans, tetrahydropyrans, and other oxygen-containing heterocycles are prevalent and dominant skeletons in drug molecules and bioactive natural product molecules. For example, functional molecules such as the macrolide Amphidinolide C1, which inhibits cancer cell proliferation, the anticancer drug Eribulin, and the expensive hepatitis C treatment Sofosbuvir, all use tetrahydrofurans and tetrahydropyrans as their basic skeletons. In traditional chemistry, the synthetic strategy for these oxygen-containing heterocycles mainly involves constructing one carbon-oxygen bond through intramolecular nucleophilic substitution reactions. In addition, some synthetic methods have been developed that utilize transition metal catalysis, free radical guidance, or electrophilic induction to convert substrates containing double, triple, or diene bonds into oxygen-containing heterocycles. Therefore, based on existing literature, the efficient and stereoselective synthesis of multi-substituted tetrahydrofurans and tetrahydropyrans, and other oxygen-containing multi-component heterocyclic compounds, remains a significant challenge.

[0003] Electrochemical synthesis differs from traditional chemical synthesis and photochemical synthesis. It utilizes electrons and electron holes to directly participate in chemical reactions, avoiding the use of chemical oxidants or reducing agents, reducing energy loss, and lowering environmental pollution. It is an important synthetic method in modern organic synthetic chemistry.

[0004] This invention discloses a novel, mild, and efficient electrochemical synthesis strategy for the rapid construction of oxo-based multi-component heterocyclic compounds mediated by halogenated free radicals. Furthermore, the introduction of halogen atoms into the target molecule during the synthesis process facilitates the subsequent synthesis of derivatized functional molecules, demonstrating potential application value. Summary of the Invention

[0005] (a) Technical problems to be solved

[0006] To address the shortcomings of existing technologies, this invention provides an electrochemical synthesis method for constructing oxo-substituted multi-component heterocyclic compounds. The electrochemical synthesis technique is disclosed, solving the technical problem that traditional chemical and photochemical synthesis methods are unable to efficiently and greenly synthesize oxo-substituted multi-component heterocyclic compounds such as tetrahydrofuran and tetrahydropyran compounds.

[0007] (II) Technical Solution

[0008] To achieve the above objectives, the present invention provides the following technical solution:

[0009] An electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds, comprising the following steps:

[0010] An alcohol compound as shown in formula (1) is added to an electrochemical reaction bottle, and then a halogen source XSalt and a solvent are added to the reaction bottle. Then, an electrode is inserted into the reaction bottle and a current or voltage is applied. After the reaction is fully carried out, an oxo-substituted polycyclic heterocyclic compound product as shown in formula (2) is obtained.

[0011] The reaction equation is as follows:

[0012]

[0013] The reaction mechanism is as follows:

[0014]

[0015] In the reaction formula and reaction mechanism:

[0016] R 1 R 2 R 3 R represents any one or more of the following: hydrogen atom, heteroaryl group, halogen, alkyl group, hydroxyl group, ether bond, ester group, and carboxyl group. 1 R 2 R 3 The groups they represent can be the same, not exactly the same, or completely different.

[0017] X represents F, Cl, Br, or I;

[0018] Y represents one or more of C, N, O, and S contained within the structural unit;

[0019] n represents a positive integer.

[0020] (III) Beneficial Effects

[0021] This invention provides an electrochemical synthesis method for constructing oxo-substituted multi-component heterocyclic compounds. Compared with existing technologies, it has the following advantages:

[0022] 1. This invention provides a method for constructing oxo-based multi-component heterocyclic compounds via an electrochemical intramolecular cyclization reaction. It mainly utilizes inexpensive metal halide salts, which lose electrons under anodic oxidation conditions and react with alkenes to obtain a three-membered ring halide salt structure. The intramolecular hydroxyl structure undergoes nucleophilic addition and ring-opening and cyclization with this structure to obtain the target product.

[0023] 2. The electrochemical synthesis method for constructing oxo-containing multi-ring heterocyclic compounds provided by this invention is based on the disclosed synthesis basis of furan ring and pyran ring. By changing the substrate chain length and heteroatom substitution, oxo-containing multi-ring heterocyclic compounds with different ring numbers can be constructed efficiently.

[0024] 3. The electrochemical synthesis method for constructing oxo-substituted multi-component heterocyclic compounds provided by this invention has the advantages of relatively easy raw material acquisition, no transition metal catalysis, batch synthesis with relatively simple chemical reactions, diverse product structures, simple operation, concise steps, high atom utilization, relatively stable chemical properties, low cost, and easy purification. Attached Figure Description

[0025] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0026] Figure 1 This is a diagram of the electrochemical synthesis reaction apparatus in an embodiment of the present invention;

[0027] Figure 2 As in Embodiment 1 of the present invention 1 H NMR spectrum;

[0028] Figure 3 This is for Embodiment 2 of the present invention. 1 H NMR spectrum;

[0029] Figure 4 This is Example 3 of the present invention. 1 H NMR spectrum;

[0030] Figure 5 This is Example 4 of the present invention. 1 H NMR spectrum;

[0031] Figure 6 This is Example 5 of the present invention. 1 H NMR spectrum;

[0032] Figure 7 This is for embodiment 6 of the present invention. 1 H NMR spectrum;

[0033] Figure 8 This is Example 7 of the present invention. 1 H NMR spectrum. Detailed Implementation

[0034] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are described clearly and completely. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0035] This application provides an electrochemical synthesis method for constructing oxo-substituted multi-component heterocyclic compounds, solving the technical problem that existing traditional chemical and photochemical synthesis methods are unable to efficiently and greenly synthesize oxo-substituted multi-component heterocyclic compounds such as tetrahydrofuran and tetrahydropyran compounds.

[0036] An electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds, comprising the following steps:

[0037] An alcohol compound as shown in formula (1) is added to an electrochemical reaction bottle, and then a halogen source XSalt and a solvent are added to the reaction bottle. Then, an electrode is inserted into the reaction bottle and a current or voltage is applied. After the reaction is fully carried out, an oxo-substituted polycyclic heterocyclic compound product as shown in formula (2) is obtained.

[0038] The reaction equation is as follows:

[0039]

[0040] The reaction mechanism is as follows:

[0041]

[0042] In the reaction equation and reaction mechanism:

[0043] R 1 R 2 R 3 R represents any one or more of the following: hydrogen atom, heteroaryl group, halogen, alkyl group, hydroxyl group, ether bond, ester group, and carboxyl group. 1 R 2 R 3 The groups they represent can be the same, not exactly the same, or completely different.

[0044] The heteroaryl group is -Ar or -Het, and the halogen is -F, -Cl, -Br or -I;

[0045] X represents F, Cl, Br, or I;

[0046] Y represents one or more of C, N, O, and S contained within the structural unit;

[0047] n represents a positive integer.

[0048] In some specific embodiments, the molar ratio of alcohol compound to halogen source is 1.0:(1.0-5.0).

[0049] In some specific embodiments, the halogen source is selected from one or more combinations of lithium iodide, sodium iodide, potassium iodide, copper iodide, manganese iodide, lithium bromide, sodium bromide, potassium bromide, copper bromide, manganese bromide, sodium chloride, potassium chloride, lithium chloride, copper chloride, ferric chloride, lithium fluoride, sodium fluoride, potassium fluoride, copper fluoride, calcium fluoride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1-fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate, hydrogen fluoride, hydrogen bromide, hydrogen chloride, hydrogen iodide, elemental fluorine, elemental bromine, elemental chlorine, and elemental iodine.

[0050] In some specific embodiments, the solvent is selected from one or more combinations of water, tetrahydrofuran, acetonitrile, benzonitrile, 1,2-dichloroethane, toluene, chlorobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, 1,4-dioxane, diethyl ether, and ethylene glycol dimethyl ether.

[0051] In some specific embodiments, the electrode includes an anode electrode and a cathode electrode, wherein the anode electrode is selected from one or more combinations of graphite, platinum, magnesium, aluminum, stainless steel, nickel, zinc, mercury, and silver.

[0052] In some specific embodiments, the cathode electrode is selected from one or more combinations of graphite, platinum, magnesium, aluminum, stainless steel, nickel, zinc, mercury, and silver.

[0053] In some specific embodiments, the anode electrode material and the cathode electrode material can be the same material or different materials.

[0054] In some specific embodiments, the current is controlled between 0.01 and 100 mA.

[0055] In some specific embodiments, the voltage is controlled between 0.01 and 10.0V.

[0056] In some specific embodiments, the reaction temperature is 25-120°C.

[0057] In some specific embodiments, the reaction time is 10-240 min.

[0058] To better understand the above technical solutions, the following will provide a detailed explanation of the technical solutions in conjunction with the accompanying drawings and specific implementation methods.

[0059] Example 1:

[0060] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0061] Depend on Figure 1As shown, 1.0 mmol of cyclopropylbenzothiophene tertiary alcohol was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium bromide and 30 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3-volt tank voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and the product was purified by column chromatography. The solvent used for column chromatography was a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:50–1:10, yielding a colorless oily product with a yield of 96%. Figure 2 , 1 H NMR(500MHz, CDCl3-d)δ8.01(d,J=8.1Hz,1H),7.93–7.86(m,1H),7.52–7.42(m,1H),7.42–7.33(m,1H),4.55–4.26(m,1H),3.69 –3.29(m,2H),2.93–2.74(m,1H),2.51–2.25(m,2H),2.16–1.92(m,1H),1.85–1.72(m,1H),1.60–1.47(m,1H),0.94–0.32(m,5H). 13 C NMR (126MHz, CDCl3-d) δ179.68,179.24,153.86,135.28,135.13,130.61,129.57,125.86,125.83,124.74,124.70,122.91,12 2.89,121.74,121.64,87.42,87.19,81.26,78.58,38.30,36.74,35.03,34.53,31.16,29.78,21.00,20.57.HRMS(ESI):Calcd forC 15 H 17 BrNOS + (M+H) + 338.0209, found 338.0212.

[0062] The reaction formula is:

[0063]

[0064] Example 2:

[0065] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0066] 1.0 mmol of phenylalkynyl tertiary alcohol compound was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium bromide and 30 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3 V cell voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and the product was purified by column chromatography using a mixture of ethyl acetate and petroleum ether (volume ratio 1:50–1:10) to obtain a colorless oily product in 88% yield. Figure 3 , 1 H NMR(400MHz, CDCl3-d)δ7.75–7.59(m,2H),7.51–7.43(m,2H),7.41–7.34(m,2H),7.34–7 .28(m,4H),4.74–4.49(m,1H),3.80–3.43(m,2H),2.74–2.47(m,2H),2.43–2.18(m,3H). 13 C NMR (101MHz, CDCl3-d) δ143.02,142.57,131.79,131.68,128.48,128.46,128.34,128.30,128.27,127.82,127.77,125.45,125 .27,91.52,90.43,85.73,85.67,82.40,81.97,80.18,77.84,43.52,42.65,35.83,35.71,31.85,30.21.HRMS(ESI):Calcd.for C 19 H 17 BrNaO + (M+Na) + 363.0355, found 363.0358.

[0067] The reaction formula is:

[0068]

[0069] Example 3:

[0070] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0071] 1.0 mmol of phenylcyanotertiary alcohol compound was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium bromide and 30 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3 V cell voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and column chromatography was performed using a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:50–1:10 to obtain a colorless oily product with a yield of 65%. Figure 4 , 1 H NMR (400MHz, CDCl3-d) δ8.02–7.90(m,2H),7.65–7.54(m,1H),7.47(t,J=7.7Hz,2H),3.24–3.09(m, 2H),3.09–3.02(m,1H),2.86–2.72(m,1H),2.62–2.47(m,1H),2.26–2.11(m,1H),1.90–1.76(m,1H). 13 CNMR(101MHz, CDCl3-d)δ136.71,133.26,133.16,128.62,128.10,128.00,71.64,66.72,51.56,47.36,34.74,34.52,27.04,26.72.HRMS(ESI):Calcd.For C 12 H 13 BrNO + (M+H) + 266.0175, found 266.0175.

[0072] The reaction formula is:

[0073]

[0074] Example 4:

[0075] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0076] 1.0 mmol of phenylbenzothiophene tertiary alcohol was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium bromide and 30 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3 V cell voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and column chromatography was performed using a mixture of ethyl acetate and petroleum ether (volume ratio 1:50–1:10) to obtain a colorless oily product with a yield of 86%. Figure 5 , 1 H NMR (400MHz, CDCl3-d) δ7.99(dd,J=8.3,5.5Hz,1H),7.81(d,J=8.0Hz,1H),7.70–7.60(m,2H),7.43(tdd,J=8.3,4.4,1.3Hz,1H),7.36–7.28(m ,3H),7.25–7.20(m,1H),3.63–3.36(m,3H),2.63(ddt,J=12.9,10.6,7. 5Hz,1H),2.36–2.10(m,1H),2.07–1.90(m,1H),1.58(d,J=12.6Hz,3H). 13 C NMR (101MHz, CDCl3-d) δ180.68,179.64,156.80,135.42,135.33,130.59,129.52,125.72,125.83 ,124.77,124.72,123.02,88.59,83.90,39.45,38.37,36.50,27.01,26.25.HRMS(ESI):Calcd.For C 19 H 18 BrNOS + (M+Na) + 387.0292, found 387.0292.

[0077] The reaction formula is:

[0078]

[0079] Example 5:

[0080] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0081] 1.0 mmol of phenylenol compound was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium iodide and 20 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3 V cell voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and column chromatography was performed using a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:50–1:10 to obtain a colorless oily product with a yield of 87%. Figure 6 , 1 H NMR(400MHz, CDCl3-d)δ7.53–7.41(m,2H),7.38–7.30(m,4H),7.30–7.24(m,3H),7.24–7.16(m,1H),6.58–6.30(m,2H ),4.59–4.16(m,1H),3.50–3.35(m,1H),3.35–3.13(m,1H),2.50–2.33(m,2H),2.32–2.05(m,1H),1.96–1.76(m,1H). 13 C NMR (101MHz, CDCl3-d) δ145.17,144.86,136.76,136.68,134.99,134.19,128.52,128.49,128.40,128.31,128.23,128.04,127.56,12 7.54,126.99,126.97,126.59,126.57,125.50,125.44,88.17,88.07,78.92,78.74,38.51,37.91,31.74,31.44.HRMS(ESI):Calcd.For C 19 H 20 IO + (M+H) + 391.0553, found 391.0556.

[0082] The reaction formula is:

[0083]

[0084] Example 6:

[0085] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0086] 1.0 mmol of methylenol compound was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium iodide and 20 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3 V cell voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and column chromatography was performed using a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:50–1:10 to obtain a colorless oily product with a yield of 89%. Figure 7 , 1 H NMR (400MHz, CDCl3-d) δ8.08–7.96(m,1H),7.92–7.83(m,1H),7.55–7.41(m,1H),7.41–7.33(m,1H),7.25–7.20(m,1H),7.12–7. 05(m,1H),7.00–6.87(m,1H),4.67–4.38(m,1H),3.54–3.15(m,4H),2.82–2.67(m,1H),2.48–2.21(m,1H),2.11–1.83(m,1H).). 13 C NMR (101MHz, CDCl3-d) δ153.53,147.73,147.33,135.46,126.99,126.91,125.98,125.23,125.19,125.12,125.08,124.62, 124.47,123.29,121.79,121.71,95.99,87.88,81.25,80.35,40.91,40.27,32.57,31.87,8.88,8.34.HRMS(ESI):Calcd.For C 18 H 16 FINOS + (M+H) + 439.9981, found 439.9982.

[0087] The reaction formula is:

[0088]

[0089] Example 7:

[0090] An electrochemical synthesis method for constructing oxo-containing multi-heterocyclic compounds, specifically:

[0091] 1.0 mmol of methylenol compound was added to a 50 mL electrochemical reaction flask under air atmosphere. 3.0 mmol of potassium iodide and 20 mL of acetonitrile solvent were added to the flask. 4 cm² graphite electrodes were inserted into the flask as the anode and cathode. A 3-volt tank voltage and current were applied to the system, and the mixture was stirred thoroughly for 1 hour. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed, and column chromatography was performed using a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:50–1:10 to obtain a colorless oily product with a yield of 68%. Figure 8 , 1 H NMR (500MHz, CDCl3-d) δ7.76–7.69(m,2H),7.45(t,J=7.5Hz,2H),7.38–7.31(m,1H),3. 45–3.35(m,2H),3.27–3.04(m,3H),1.92(s,1H),1.90–1.79(m,1H),1.59–1.49(m,1H).. 13 C NMR(125MHz, CDCl3-d)δ132.35,129.12,128.35,127.35,115.06,86.60,78.98,40.01,31.30,28.41.HRMS(ESI):Calcd.For C 12 H 13 IN2NaO + (M+Na) + 350.9970, found 350.9974.

[0092] The reaction formula is:

[0093]

[0094] In summary, compared with existing technologies, it has the following beneficial effects:

[0095] 1. This invention provides a method for constructing oxo-based multi-component heterocyclic compounds via an electrochemical intramolecular cyclization reaction. It mainly utilizes inexpensive metal halide salts, which lose electrons under anodic oxidation conditions and react with alkenes to obtain a three-membered ring halide salt structure. The intramolecular hydroxyl structure undergoes nucleophilic addition and ring-opening and cyclization with this structure to obtain the target product.

[0096] 2. The electrochemical synthesis method for constructing oxo-containing multi-ring heterocyclic compounds provided by this invention is based on the disclosed synthesis basis of furan ring and pyran ring. By changing the substrate chain length and heteroatom substitution, oxo-containing multi-ring heterocyclic compounds with different ring numbers can be constructed efficiently.

[0097] 3. The electrochemical synthesis method for constructing oxo-substituted multi-component heterocyclic compounds provided by this invention has the advantages of relatively easy raw material acquisition, no transition metal catalysis, batch synthesis with relatively simple chemical reactions, diverse product structures, simple operation, concise steps, high atom utilization, relatively stable chemical properties, low cost, and easy purification.

[0098] It should be noted that, in this document, relational terms such as "first" and "second" are used only to distinguish one entity or operation from another, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Furthermore, the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a process, method, article, or apparatus. Without further limitations, an element defined by the phrase "comprising one..." does not exclude the presence of other identical elements in the process, method, article, or apparatus that includes said element.

[0099] 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 spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. An electrochemical synthesis method for constructing oxo-substituted multi-cyclic heterocyclic compounds, characterized in that, The specific steps are as follows: An alcohol compound as shown in formula (1) is added to an electrochemical reaction bottle, and then a halogen source X Salt and a solvent are added to the reaction bottle. Then, an electrode is inserted into the reaction bottle and a current or voltage is applied. After the reaction is fully carried out, an oxo-substituted polycyclic heterocyclic compound product as shown in formula (2) is obtained. The reaction equation is as follows: Among them, R 1 R 2 R 3 R represents any one or more of the following: hydrogen atom, heteroaryl group, halogen, alkyl group, hydroxyl group, ether bond, ester group, and carboxyl group. 1 R 2 R 3 The groups they represent can be the same, not exactly the same, or completely different. X represents F, Cl, Br, or I; Y represents one or more of C, N, O, and S contained within the structural unit; n represents a positive integer.

2. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The heteroaryl group is -Ar or -Het, and the halogen is -F, -Cl, -Br or -I.

3. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The molar ratio of the alcohol compound to the halogen source is 1.0:(1.0-5.0).

4. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The halogen source is selected from one or more combinations of lithium iodide, sodium iodide, potassium iodide, copper iodide, manganese iodide, lithium bromide, sodium bromide, potassium bromide, copper bromide, manganese bromide, sodium chloride, potassium chloride, lithium chloride, copper chloride, ferric chloride, lithium fluoride, sodium fluoride, potassium fluoride, copper fluoride, calcium fluoride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1-fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate, hydrogen fluoride, hydrogen bromide, hydrogen chloride, hydrogen iodide, elemental fluorine, elemental bromine, elemental chlorine, and elemental iodine.

5. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The solvent is selected from one or more combinations of water, tetrahydrofuran, acetonitrile, benzonitrile, 1,2-dichloroethane, toluene, chlorobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, 1,4-dioxane, diethyl ether, and ethylene glycol dimethyl ether.

6. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The electrode includes an anode electrode and a cathode electrode. The anode electrode and the cathode electrode are selected from one or more combinations of graphite, platinum, magnesium, aluminum, stainless steel, nickel, zinc, mercury, and silver. The anode electrode material and the cathode electrode material can be the same material or different materials.

7. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The current is controlled between 0.01 and 100 mA.

8. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The voltage is controlled between 0.01 and 10.0V.

9. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, During the preparation of the product, the reaction temperature is 25-120℃.

10. The electrochemical synthesis method for constructing oxo-substituted multi-heterocyclic compounds as described in claim 1, characterized in that, The reaction time during product preparation is 10-240 min.

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