A β-ketosulfone compound and its synthesis method
The synthesis of β-ketosulfone compounds through electrochemical redox catalysis solves the environmental and cost problems of traditional methods, achieves efficient, green and sustainable synthesis, and is suitable for the synthesis of a variety of drugs.
Patent Information
- Application Number
- CN202510287510.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-12
- Publication Date
- 2025-09-30
- Estimated Expiration
- 2045-03-12
AI Technical Summary
Existing synthesis methods for β-ketosulfone compounds require the use of complex starting materials, long reaction steps, and the use of unstable oxidants or transition metal catalysts, leading to environmental concerns and high costs.
The invention adopts an enol ester compound and a sulfonyl hydrazide compound to synthesize a beta-ketosulfone compound through electrochemical redox catalysis, avoids using an external oxidant or reducing agent, and uses an electrochemical method to carry out the reaction.
It achieves green, sustainable and efficient synthesis of β-ketosulfone compounds, reduces chemical waste generation, is suitable for the synthesis of β-ketosulfone compounds with various substituents, and expands the application prospects of drug synthesis.
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Figure CN119876974B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of chemical synthesis, and in particular to a beta-ketosulfone compound and a synthesis method thereof. Background Art
[0002] Among various sulfone-containing compounds, β-ketosulfones and related sulfone compounds have attracted considerable attention due to their excellent biological activities, such as anti-hepatitis, antibacterial, antifungal, and non-nucleoside inhibitors. Furthermore, β-ketosulfones possess multifunctional functional groups, such as sulfonyl, carbonyl, and active methylene groups, making them amenable to various synthetic manipulations. Traditionally, β-ketosulfone derivatives have been synthesized by constructing C-S or C-C bonds, such as the alkylation of α-haloketones or the oxidation of β-carbonyl sulfides or β-hydroxysulfones. However, these methods typically require complex starting materials, lengthy reaction steps, and the use of unstable, highly active oxidants or transition metal catalysts, which can lead to environmental concerns, metal residues, and high costs. Given the current state of research, it is necessary to develop a simple and sustainable catalytic system. Summary of the Invention
[0003] The main purpose of the present invention is to propose a β-ketosulfone compound and a synthesis method thereof, which uses an enol ester compound and a sulfonylhydrazide compound to synthesize the β-ketosulfone compound through electrochemical redox catalysis, has the advantages of being green, sustainable, highly efficient and under mild conditions, and avoids the use of additional oxidants or reducing agents.
[0004] To achieve the above object, the present invention provides a β-ketosulfone compound, which is synthesized from an enol ester compound and a sulfonylhydrazide compound through electrochemical redox catalysis.
[0005] The structural formula of the β-ketosulfone compound is:
[0006] The structural formula of the enol ester compound is:
[0007] The structural formula of the sulfonylhydrazide compound is:
[0008] Preferably, the synthetic route of the β-ketosulfone compound is as follows:
[0009]
[0010] Preferably, R1 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen, or sulfur atoms; R2 is a hydrogen atom, a methyl group, or an unsubstituted straight-chain alkane; and R3 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen, or sulfur atoms, or a substituted or unsubstituted straight-chain alkyl group.
[0011] Preferably, the preparation method of the β-ketosulfone compound comprises the following steps:
[0012] An enol ester compound, a sulfonylhydrazide compound, an electrolyte, sodium carbonate, and an acetonitrile aqueous solution are added to a closed system, and then electrodes are installed, with graphite as the anode and a platinum sheet as the cathode. After the electrodes are installed, electrochemical oxidation is performed. After the reaction is completed, post-treatment is performed to obtain a β-ketosulfone compound.
[0013] Preferably, the molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte, and the sodium carbonate is 1:1.2-2:1-1.2:2.5-3.
[0014] More preferably, the molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte, and the sodium carbonate is 1:1.5:1:3.
[0015] Preferably, the electrolyte is at least one of tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium chloride, and tetraethylammonium bromide.
[0016] Preferably, the volume ratio of acetonitrile to water in the acetonitrile aqueous solution is 15-20:1.
[0017] Preferably, the current during the electrochemical oxidation process is 5-15 mA, the reaction temperature is room temperature, and the reaction time is 3-5 h.
[0018] Compared with the prior art, the present invention has the following beneficial effects:
[0019] The present invention synthesizes a β-ketosulfone compound from an enol ester compound and a sulfonylhydrazide compound via electrochemical redox catalysis, avoiding the use of complex starting materials, shortening the reaction steps, and improving synthesis efficiency. The electrochemical redox catalysis method avoids the use of external oxidants or reducing agents used in traditional synthesis, reduces the generation of chemical waste, conforms to the principles of green chemistry, and is highly environmentally friendly. The synthesis method of the present invention is suitable for synthesizing β-ketosulfone compounds with a variety of different substituents, expanding their application prospects in pharmaceutical synthesis, and has good application prospects and industrialization potential. BRIEF DESCRIPTION OF THE DRAWINGS
[0020] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the description of the prior art. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other relevant drawings can be obtained based on these drawings without paying any creative work.
[0021] Figure 1 The β-ketosulfone compound prepared in Example 1 of the present invention 1 HNMR spectrum;
[0022] Figure 2 The β-ketosulfone compound prepared in Example 1 of the present invention 13 CNMR spectrum;
[0023] Figure 3 The β-ketosulfone compound prepared in Example 2 of the present invention 1 HNMR spectrum;
[0024] Figure 4 The β-ketosulfone compound prepared in Example 2 of the present invention 13 CNMR spectrum;
[0025] Figure 5 The β-ketosulfone compound prepared in Example 3 of the present invention 1 HNMR spectrum;
[0026] Figure 6 The β-ketosulfone compound prepared in Example 3 of the present invention 13 CNMR spectrum;
[0027] Figure 7 The β-ketosulfone compound prepared in Example 4 of the present invention 1 HNMR spectrum;
[0028] Figure 8 The β-ketosulfone compound prepared in Example 4 of the present invention 13 CNMR spectrum;
[0029] Figure 9 The β-ketosulfone compound prepared in Example 5 of the present invention 1 HNMR spectrum;
[0030] Figure 10 The β-ketosulfone compound prepared in Example 5 of the present invention 13 CNMR spectrum.
[0031] The purpose, features and advantages of the present invention will be further described with reference to the accompanying drawings and in conjunction with the embodiments. DETAILED DESCRIPTION
[0032] To avoid redundancy, the items used in the following examples are all commercially available products unless otherwise specified, and the methods used are all conventional methods unless otherwise specified.
[0033] Example 1
[0034] A method for preparing a β-ketosulfone compound comprises the following steps:
[0035] S1. At -78°C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, followed by dropwise addition of 0.61 g of n-butyllithium (9.6 mmol), and the mixture was stirred at -78°C for 30 minutes; 0.96 g of acetophenone (8 mmol) was then added to the reaction mixture, and the mixture was stirred at -78°C for 45 minutes, followed by addition of 1.63 g of acetic anhydride (16 mmol), and the reaction mixture was stirred at -78°C for 30 minutes, followed by reaction at room temperature for 1.5 h. After completion of the reaction, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain an enol ester compound;
[0036] S2. At 0°C, under N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of a tetrahydrofuran solution containing 2.07 g of 4-methoxybenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether:ethyl acetate=10:1) to obtain 4-methoxybenzenesulfonylhydrazide.
[0037] S3, 40.5mg enol ester compound (0.25mmol), 75.81mg 4-methoxybenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mLMeCN / H2O aqueous solution (the volume ratio of MeCN and water is 19:1) are mixed evenly and added to a 10mL small glass bottle with thread, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After completion of the reaction, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times. After drying, the organic phase is spin-dried and column-passed at normal pressure using petroleum ether / ethyl acetate = 8:1 to obtain a β-ketosulfone compound.
[0038] The structural formula of the β-ketosulfone compound obtained in this example is The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 1 As shown, 1 HNMR (400MHz, CDCl3) δ7.97–7.92(m,2H),7.76(d,J=8.3Hz,2H),7.65–7.59(m ,1H),7.48(t,J=7.8Hz,2H),7.33(d,J=8.0Hz,2H),4.71(s,2H),2.44(s,3H).
[0039] The β-ketosulfone compound obtained in this example 13 CNMR spectrum such as Figure 2 As shown, 13 CNMR (100MHz, CDCl3) δ188.1,145.4,135.8,134.3,129.8,129.3,128.8,128.6,63.6,21.7.
[0040] Example 2
[0041] A method for preparing a β-ketosulfone compound comprises the following steps:
[0042] S1. At -80°C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, followed by dropwise addition of 0.61 g of n-butyllithium (9.6 mmol), and the mixture was stirred at -80°C for 30 minutes; 0.96 g of acetophenone (8 mmol) was then added to the reaction mixture, and the mixture was stirred at -78°C for 45 minutes, followed by addition of 1.63 g of acetic anhydride (16 mmol), and the reaction mixture was stirred at -80°C for 30 minutes, followed by reaction at room temperature for 1.5 h. After the reaction was complete, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with salt water. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain an enol ester compound;
[0043] S2. At 0°C, under N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of a tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether:ethyl acetate=10:1) to obtain 4-methylbenzenesulfonylhydrazide.
[0044] S3, 40.5mg enol ester compound (0.25mmol), 69.8mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN and water is 15:1) are mixed evenly and added into a 10mL small glass bottle with thread, stir bar is added, then electrode is installed, graphite is anode, platinum sheet is cathode, current 10mA, stirring reaction 4h at room temperature. After completion of the reaction, transfer to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, then washed 3 times with water, the organic phase is spin-dried after drying, and petroleum ether / ethyl acetate=8:1 normal pressure column is used to obtain β-ketosulfone compound.
[0045] The structural formula of the β-ketosulfone compound obtained in this example is
[0046] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 3 As shown, 1 HNMR (400MHz, CDCl3) δ7.97–7.92(m,2H),7.76(d,J=8.3Hz,2H),7.65–7.59(m ,1H),7.48(t,J=7.8Hz,2H),7.33(d,J=8.0Hz,2H),4.71(s,2H),2.44(s,3H).
[0047] The β-ketosulfone compound obtained in this example 13 CNMR spectrum such as Figure 4 As shown, 13 CNMR (100MHz, CDCl3) δ188.1,145.4,135.8,134.3,129.8,129.3,128.8,128.6,63.6,21.7.
[0048] Example 3
[0049] A method for preparing a β-ketosulfone compound comprises the following steps:
[0050] S1. At -78 ° C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, followed by the dropwise addition of 0.61 g of n-butyl lithium (9.6 mmol), and the mixture was stirred at -78 ° C for 30 minutes. 1.5 g of 4-(trifluoromethyl)acetophenone (8 mmol) was then added to the reaction mixture, and the mixture was stirred at -78 ° C for 45 minutes. 1.63 g of acetic anhydride (16 mmol) was then added, and the reaction mixture was stirred at -78 ° C for 30 minutes. The reaction mixture was subsequently stirred at room temperature for 2 h. After the reaction was complete, the mixed solution was poured into a saturated sodium bicarbonate solution (100 mL), the reaction mixture was extracted with ethyl acetate (60 mL), and the combined organic layer was rinsed with brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain an enol ester compound;
[0051] S2. At 0°C, under N2 atmosphere, add 1.5 g of hydrazine monohydrate (30 mmol) dropwise to 50 mL of a tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stir for 1 h. After the reaction is complete, evaporate the solvent, extract the residue with dichloromethane (3×20 mL), wash the combined organic layer with water and saturated brine, and dry over anhydrous sodium sulfate. Evaporate the organic solvent under reduced pressure, and purify on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methylbenzenesulfonyl hydrazide;
[0052] S3, 57.5mg enol ester compound (0.25mmol), 69.84mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), MeCN / H2O=20:1 (total 5mL) in a threaded 10mL small glass bottle, add a stirrer, then install electrodes, graphite as anode, platinum sheet as cathode, current 10mA, stir the reaction at room temperature for 4h. After completion of the reaction, transfer to a 25mL round-bottom flask, spin-dry the mixed system, add ethyl acetate, then wash 3 times with water, dry the organic phase and spin-dry, use petroleum ether / ethyl acetate=8:1 normal pressure column to obtain β-ketosulfone compound.
[0053] The structural formula of the β-ketosulfone compound obtained in this example is
[0054] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 5 As shown, 1HNMR (400MHz, CDCl3) δ8.07(d,J=8.2Hz,2H),7.75(d,J=3.5Hz,2H),7.73(d,J=3.5Hz,2H),7.35(d,J=8.0Hz,2H),4.73(s,2H),2.45(s,3H).
[0055] The β-ketosulfone compound obtained in this example 13 CNMR spectrum such as Figure 6 As shown, 13 CNMR (100MHz, CDCl3) δ 187.4, 145.7, 138.3, 135.4 (t, JC-F = 32.7Hz), 130.0, 129.7, 128.5, 125.9 (q, JC-F = 11.2Hz), 124.7, 124.0, 63.9, 21.7.
[0056] Example 4
[0057] A method for preparing a β-ketosulfone compound comprises the following steps:
[0058] S1. At -78 ° C., under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, followed by dropwise addition of 0.61 g of n-butyllithium (9.6 mmol), and the mixture was stirred at -78 ° C. for 30 minutes; 1.01 g of 2-acetylthiophene (8 mmol) was then added to the reaction mixture, and the mixture was stirred at -78 ° C. for 45 minutes, followed by addition of 1.63 g of acetic anhydride (16 mmol), and the reaction mixture was stirred at -78 ° C. for 30 minutes, and the reaction mixture was subsequently reacted at room temperature for 1.5 h. After the reaction was complete, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with salt water. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain an enol ester compound;
[0059] S2. At 0°C, under N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to a 50 mL tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether:ethyl acetate=10:1) to obtain 4-methylbenzenesulfonyl hydrazide.
[0060] S3, 42mg enol ester compound (0.25mmol), 69.8mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN and water is 19:1) are mixed evenly and added to a 10mL small glass bottle with thread, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After completion of the reaction, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times. After drying, the organic phase is spin-dried and column-passed at normal pressure using petroleum ether / ethyl acetate = 8:1 to obtain a β-ketosulfone compound.
[0061] The structural formula of the β-ketosulfone compound obtained in this example is
[0062] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 7 As shown, 1 HNMR (400MHz, CDCl3) δ7.81(d,J=3.8Hz,1H),7.75(t,J=5.5Hz,3H),7.33(d,J=8.1Hz,2H),7.16(t,J=4.4Hz,1H),4.61(s,2H),2.43(s,3H).
[0063] The β-ketosulfone compound obtained in this example 13 CNMR spectrum such as Figure 8 As shown, 13 CNMR (100MHz, CDCl3) δ180.3,145.4,143.1,136.4,135.4,135.3,129.8,128.7,128.6,64.6,21.7.
[0064] Example 5
[0065] A method for preparing a β-ketosulfone compound comprises the following steps:
[0066] S1, at-78 ℃, N2 atmosphere, in a dry round-bottom flask, add 20mL tetrahydrofuran (THF) and 97.8mg diisopropylamine (9.6mmol), then drip 0.61g n-butyllithium (9.6mmol), the mixture was stirred at-78 ℃ for 30 minutes; Then 1.19g 1-tetralone (8mmol) was added to the reaction mixture, and stirred at-78 ℃ for 45 minutes, then 1.63g diacetic anhydride (16mmol) was added, the reaction mixture was stirred at-78 ℃ for 30 minutes, and subsequently the reaction mixture was reacted at room temperature for 1.5h. After the reaction was completed, the mixed solution was poured into 100mL saturated sodium bicarbonate solution, the reaction mixture was extracted with 60mL ethyl acetate, and the organic layer combined was rinsed with salt solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain an enol ester compound;
[0067] S2. At 0°C, under N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to a 50 mL tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether:ethyl acetate=10:1) to obtain 4-methylbenzenesulfonyl hydrazide.
[0068] S3, 47mg enol ester compound (0.25mmol), 75.81mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN and water is 19:1) are mixed evenly and added to a 10mL small glass bottle with thread, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After completion of the reaction, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times. After drying, the organic phase is spin-dried and column-passed at normal pressure using petroleum ether / ethyl acetate = 8:1 to obtain a β-ketosulfone compound.
[0069] The structural formula of the β-ketosulfone compound obtained in this example is The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 9 As shown, 1HNMR (400 MHz, CDCl3) δ7.98 (d, J = 7.9 Hz, 1H), 7.79 (d, J = 8.1 Hz, 2H), 7.52 (t, J = 7.5 Hz, 1H), 7.36 (d, J = 8.0 Hz, 2H), 7.31 (t, J = 7.6 Hz, 1H), 7.27 (d, J = 6.8 Hz, 1H), 4.09 (t, J = 5.6 Hz, 1H), 3.57–3.47 (m, 1H), 2.98 (dt, J = 16.9, 5.3 Hz, 1H), 2.87 (dq, J = 16.5, 5.5 Hz, 1H), 2.65 (ddt, J = 14.7, 10.0, 5.0 Hz, 1H), 2.45 (s, 3H). 13 CNMR spectrum such as Figure 10 As shown, 13 CNMR (100MHz, CDCl3) δ188.7,145.1,143.6,135.9,134.4,131.7,129.6,129.1,128.9,127.9,127.0,69.6,26.5,23.6,21.7.
[0070] The above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Those skilled in the art will readily appreciate that the present invention is susceptible to various modifications and variations. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the present invention shall be included within the scope of the present invention.
Claims
1. A method for synthesizing β-ketosulfone compounds by electrochemical redox catalysis, characterized in that: The synthetic route of the β-ketosulfone compound is as follows: ， The R1 is one of phenyl, trifluoromethylphenyl, and thienyl; the R2 is a hydrogen atom; and the R3 is one of methylphenyl and methoxyphenyl.
2. The method according to claim 1, characterized in that The steps include: An enol ester compound, a sulfonylhydrazide compound, tetrabutylammonium tetrafluoroborate, sodium carbonate, and an acetonitrile aqueous solution are added to a closed system, and then electrodes are installed, with graphite as the anode and a platinum sheet as the cathode. After the electrodes are installed, electrochemical oxidation is performed. After the reaction is completed, post-treatment is performed to obtain a β-ketosulfone compound.
3. The method according to claim 2, wherein: The molar ratio of the enol ester compound, the sulfonyl hydrazide compound, tetrabutylammonium tetrafluoroborate and sodium carbonate is 1:1.2-2:1-1.2:2.5-3.
4. The method according to claim 2, wherein: The molar ratio of the enol ester compound, the sulfonyl hydrazide compound, tetrabutylammonium tetrafluoroborate and sodium carbonate is 1:1.5:1:
3.
5. The method according to claim 2, wherein: The volume ratio of acetonitrile to water in the acetonitrile aqueous solution is 15-20:1.