Synthesis method of polysubstituted pyrazole compound

Abstract

The invention relates to the technical field of organic synthesis, in particular to a synthesis method of a polysubstituted pyrazole compound, which comprises the following steps: adding 0.6 mmol of aryl diazonium salt, 0.9 mmol of ketene, 0.5 ml of acid and 0.3 mmol of electrolyte into a 10ml three-necked bottle, and adding 6ml of solvent into the three-necked bottle for dissolving; taking a carbon rod as an anode and a platinum sheet as a cathode, stirring and reacting, monitoring the reaction process by using thin layer chromatography, and extracting the mixture by using ethyl acetate after the reaction is finished; drying an organic layer of the mixture by adopting anhydrous sodium sulfate, carrying out reduced-pressure spin-drying on a solvent, and purifying residues by virtue of column chromatography, so as to obtain a target product. A series of polysubstituted pyrazole compounds are directly synthesized by continuously generating two free radicals through electrochemical reduction of aryl diazonium salt, the polysubstituted pyrazole compounds can be directly and orderly constructed without transition metal or additional redox agents, and the polysubstituted pyrazole compounds are environment-friendly, efficient and high in atom economy.

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, and in particular to a method for synthesizing a polysubstituted pyrazole compound. Background Art

[0002] Polysubstituted pyrazoles are an important structural framework that are widely used in pharmaceuticals, agrochemicals, functional materials, ligands, etc. Although progress has been made in the synthesis of polysubstituted pyrazole compounds in recent years, their efficient synthesis remains a major challenge and difficulty in organic synthesis.

[0003] Polysubstituted pyrazoles are important structural units that are widely used in various fields, including medicine, agrochemicals, functional materials, etc. There are two main strategies for the traditional synthesis of polysubstituted pyrazoles: first, functionalization of the pyrazole skeleton; second, assembly of new pyrazole rings from acyclic precursors. However, these methods usually require the use of transition metal catalysts, equivalent redox agents, harsh reaction conditions, and numerous steps, making them difficult to apply in actual synthesis.

[0004] Therefore, ensuring the ordered addition of the two radicals generated from aryl diazonium salts to olefins to form a single product is a major challenge. Summary of the invention

[0005] The purpose of the present invention is to provide a method for synthesizing polysubstituted pyrazole compounds, aiming to solve the problems that the existing methods for synthesizing polysubstituted pyrazole compounds require the use of transition metal catalysts or redox agents, have harsh reaction conditions and numerous steps, and are difficult to apply in actual synthesis.

[0006] To achieve the above object, the present invention provides a method for synthesizing a polysubstituted pyrazole compound, comprising the following steps:

[0007] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acid and 0.3 mmol of electrolyte were added to a 10 ml three-necked flask, and 6 ml of solvent was added thereto to dissolve;

[0008] A carbon rod was used as an anode and a platinum sheet was used as a cathode to carry out a stirring reaction, and the reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate;

[0009] The organic layer of the mixture is dried over anhydrous sodium sulfate, the solvent is evaporated under reduced pressure, and the residue is purified by column chromatography to obtain the target product.

[0010] Wherein, the acid comprises one or more of acetic acid, trifluoromethanesulfonic acid and trifluoroacetic acid.

[0011] Wherein, the electrolyte includes one or more of tetrabutylammonium hexafluorophosphonate, tetraethylammonium hexafluorophosphonate, tetrabutylammonium tetrafluoroborate and tetrabutylammonium iodide.

[0012] Wherein, the solvent includes acetonitrile, dimethyl sulfoxide, and a mixture of dimethyl sulfoxide and water.

[0013] The stirring reaction conditions include a constant current of 5-20 mA, a reaction temperature of 10-40 degrees Celsius, and a stirring reaction time of 0.5-3 hours.

[0014] The invention discloses a method for synthesizing a polysubstituted pyrazole compound, and relates to the technical field of organic synthesis, and particularly relates to a method for synthesizing a polysubstituted pyrazole compound. The method comprises the following steps: adding 0.6 mmol of an aryl diazonium salt, 0.9 mmol of an ene ketone, 0.5 ml of an acid and 0.3 mmol of an electrolyte to a 10 ml three-necked bottle, and adding 6 ml of a solvent to dissolve the aryl diazonium salt; using a carbon rod as an anode and a platinum sheet as a cathode to stir the reaction, using thin layer chromatography to monitor the reaction process, and extracting the mixture with ethyl acetate after the reaction is completed; drying the organic layer of the mixture with anhydrous sodium sulfate, and performing vacuum evaporation. The dry solvent is prepared and the residue is purified by column chromatography to obtain the target product. The method uses aromatic diazonium salt as a double synthon under mild electrochemical conditions, and continuously generates two free radicals through the electrochemical reduction of aromatic diazonium salt to directly synthesize a series of polysubstituted pyrazole compounds. Polysubstituted pyrazole compounds can be directly and orderly constructed without transition metals or external redox agents. The method is environmentally friendly, efficient and highly atom-economical, and solves the problems of existing methods for synthesizing polysubstituted pyrazole compounds, which require the use of transition metal catalysts or redox agents, have harsh reaction conditions and numerous steps, and are difficult to apply in actual synthesis. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0016] Figure 1 The present invention provides a flow chart of a method for synthesizing a polysubstituted pyrazole compound.

[0017] Figure 2 is a schematic diagram of a general method for synthesizing a polysubstituted pyrazole compound provided by the present invention, wherein R 1 , R 2 , R 3 = aromatic group, alkyl group, etc.

[0018] Figure 3 The structural formula of 3-ethyl-5-methyl-1,4-diphenyl-1H-pyrazole (3a) is shown in FIG.

[0019] Figure 4 The structural formula of 3,5-dimethyl-1,4-diphenyl-1H-pyrazole (3b) is shown.

[0020] Figure 5 It is the structural formula of 3-methyl-1,4-diphenyl-5-propyl-1H-pyrazole (3c).

[0021] Figure 6 The structural formula of 5-butyl-4-(cyclohexa-1,5-dien-1-yl)-3-methyl-1-phenyl-1H-pyrazole (3d) is shown.

[0022] Figure 7 This is the structural formula of 3-methyl-1,4,5-triphenyl-1H-pyrazole (3e).

[0023] Figure 8 It is the structural formula diagram of 3-methyl-1,4-diphenyl-5-(p-tolyl)-1H-pyrazole (3f).

[0024] Fig. 9 The structural formula of 5-(4-methoxyphenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3g) is shown in FIG.

[0025] Fig.10 This is the structural formula of 5-(4-fluorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3h).

[0026] Fig.11 The structural formula of 5-(4-chlorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3i) is shown in FIG.

[0027] Fig.12 The structural formula of 5-(3-bromo-4-fluorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3j) is shown.

[0028] Fig.13 The structural formula of 5-(5-bromofuran-2-yl)-3-methyl-1,4-diphenyl-1H-pyrazole (3k) is shown.

[0029] Fig.14 The structural formula of 5-(4-bromothiophen-2-yl)-3-methyl-1,4-diphenyl-1H-pyrazole (3l) is shown.

[0030] Fig.15 It is the structural formula diagram of 3-methyl-5-(naphthalen-2-yl)-1,4-diphenyl-1H-pyrazole (3m).

[0031] Fig.16 This is the structural formula of 3-ethyl-5-methyl-1,4-di-p-tolyl-1H-pyrazole (3n).

[0032] Fig.17 The structural formula of 1,4-bis(4-(tert-butyl)phenyl)-3-ethyl-5-methyl-1H-pyrazole (3o) is shown in FIG.

[0033] Fig.18 It is the structural formula diagram of 1,4-bis(4-chlorophenyl)-3-ethyl-5-methyl-1H-pyrazole (3p).

[0034] Fig.19 The structural formula of 3-ethyl-5-methyl-1,4-bis(4-(trifluoromethyl)phenyl)-1H-pyrazole (3q) is shown.

[0035] Fig. 20 The structural formula of methyl 4-(5-ethyl-1-(4-(2-methoxy-2-oxoethyl)phenyl)-3-methyl-1H-pyrazol-4-yl)benzoate (3r) is shown.

[0036] Fig.21 It is a structural formula diagram of 5-ethyl-3-methyl-1,4-di(naphthalen-2-yl)-1H-pyrazole (3s).

[0037] Fig. 22 The structural formula of 1,4-bis(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-ethyl-3-methyl-1H-pyrazole (3t) is shown. DETAILED DESCRIPTION

[0038] Embodiments of the present invention are described in detail below, examples of which are shown in the accompanying drawings, wherein the same or similar reference numerals throughout represent the same or similar elements or elements having the same or similar functions. The embodiments described below with reference to the accompanying drawings are exemplary and are intended to be used to explain the present invention, and should not be construed as limiting the present invention.

[0039] See also Figures 1 to 22 , the present invention provides a method for synthesizing a polysubstituted pyrazole compound, comprising the following steps;

[0040] S1: 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acid and 0.3 mmol of electrolyte were added to a 10 ml three-necked flask, and 6 ml of solvent was added to dissolve;

[0041] In an embodiment of the present invention, the acid includes one or more of acetic acid, trifluoromethanesulfonic acid and trifluoroacetic acid, the electrolyte includes one or more of tetrabutylammonium hexafluorophosphonate, tetraethylammonium hexafluorophosphonate, tetrabutylammonium tetrafluoroborate and tetrabutylammonium iodide, and the solvent includes acetonitrile, dimethyl sulfoxide, or a mixture of dimethyl sulfoxide and water;

[0042] Specifically, 0.6 mmol of aromatic diazonium salt, 0.9 mmol of enone, 0.5 ml of acid (acetic acid, trifluoromethanesulfonic acid or trifluoroacetic acid, etc.), and 0.3 mmol of electrolyte (tetrabutylammonium hexafluorophosphonate, tetraethylammonium hexafluorophosphonate, tetrabutylammonium tetrafluoroborate or tetrabutylammonium iodide, etc.) are added to a 10 ml three-necked flask, and 6 ml of solvent (acetonitrile, dimethyl sulfoxide, a mixture of dimethyl sulfoxide and water, etc.) is added to dissolve.

[0043] S2 uses a carbon rod as an anode and a platinum sheet as a cathode to carry out a stirring reaction, and uses thin layer chromatography to monitor the reaction progress. After the reaction is completed, the mixture is extracted with ethyl acetate;

[0044] In an embodiment of the present invention, the stirring reaction conditions include a constant current of 5-20 mA, a reaction temperature of 10-40 degrees Celsius, and a stirring reaction time of 0.5-3 hours.

[0045] Specifically, a carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at a constant current of 5-20 mA at 10-40 degrees Celsius for 0.5-3 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml).

[0046] S3: drying the organic layer of the mixture with anhydrous sodium sulfate, drying the solvent under reduced pressure, and purifying the residue by column chromatography to obtain the target product.

[0047] In the present embodiment, the organic layer of the mixture is dried over anhydrous sodium sulfate, the solvent is evaporated under reduced pressure, and the residue is purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:15-40) to obtain the target product.

[0048] In order to better understand the present technical solution, the following embodiments are provided for further explanation:

[0049] Preparation and characterization of polysubstituted pyrazole compounds:

[0050] Example 1

[0051] Preparation and characterization of 3-ethyl-5-methyl-1,4-diphenyl-1H-pyrazole (3a):

[0052] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, and 6 ml of acetonitrile was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 15 mA constant current at 40 degrees Celsius for 2 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:30) to obtain the target product 3a.

[0053] Yellow oil (78%, 61.4 mg). 1 H NMR (400MHz, Chloroform-d) δ750-7.48 (m, 4H), 7.46-7.41 (m, 3H), 7.35-7.31 (m, 3H), 2.72 (q, J=7.6Hz, 2H), 2.31 (s, 3H), 0.91 (t, J=7.6Hz, 3H). 13 C NMR (126MHz, Chloroform-d) δ147.20, 142.77, 139.94, 133.86, 129.85, 129.34, 128 .62, 128.18, 126.82, 125.87, 120.43, 18.17, 13.83, 12.52.HRMS(m / z)(ESI):calcd for C 18 H 19 N2[M+H] + 263.1543, found 263.1550.

[0054] Example 2

[0055] Preparation and characterization of 3,5-dimethyl-1,4-diphenyl-1H-pyrazole (3b):

[0056] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, and 6 ml of acetonitrile was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 15 mA constant current at 40 degrees Celsius for 2 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:30) to obtain the target product 3a.

[0057] Yellow oil (78%, 61.4 mg). 1H NMR (400MHz, Chloroform-d) δ750-7.48 (m, 4H), 7.46-7.41 (m, 3H), 7.35-7.31 (m, 3H), 2.72 (q, J=7.6Hz, 2H), 2.31 (s, 3H), 0.91 (t, J=7.6Hz, 3H). 13 C NMR (126MHz, Chloroform-d) δ147.20, 142.77, 139.94, 133.86, 129.85, 129.34, 128 .62, 128.18, 126.82, 125.87, 120.43, 18.17, 13.83, 12.52.HRMS(m / z)(ESI):calcd for C 18 H 19 N2[M+H] + 263.1543, found 263.1550.

[0058] Example 3

[0059] Preparation and characterization of 3,5-dimethyl-1,4-diphenyl-1H-pyrazole (3b):

[0060] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetraethylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, 6 ml of dimethyl sulfoxide was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 10 mA constant current at 35 degrees Celsius for 1.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:25) to obtain the target product 3b.

[0061] Yellow oil (77%, 57.4 mg). 1 H NMR (400MHz, Chloroform-d) δ7.49-7.45(m, 5H), 7.44-7.38(m, 2H), 7.34-7.31(m, 3H), 2.35(s, 3H), 2.31(s, 3H). 13 CNMR (126MHz, Chloroform-d) δ147.29, 140.00, 136.54, 133.92, 129.70, 129.22 ,128.61,127.60,126.60,125.12,121.05,12.79,11.96.HRMS(m / z)(ESI):calcd for C17 H 17 N2[M+H] + 249.1386, found 249.1392.

[0062] Example 4

[0063] Preparation and characterization of 3-methyl-1,4-diphenyl-5-propyl-1H-pyrazole (3c):

[0064] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, and 6 ml of acetonitrile was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 10 mA constant current at 35 degrees Celsius for 2 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether = 1:30) to obtain the target product 3c.

[0065] Yellow oil (72%, 59.7 mg). 1 H NMR (400MHz, Chloroform-d) δ7.52-7.47(m, 4H), 7.45-7.41(m, 2H), 7.38-7.30( m, 4H), 2.70-2.66 (m, 2H), 2.28 (s, 2H), 1.65-1.60 (m, 3H), 0.91 (t, J=7.2Hz, 3H). 13 C NMR (126MHz, Chloroform-d) δ151.44, 139.99, 136.58, 134.02, 129.87, 129.21, 128.59 ,127.56,126.68,125.14,120.87,29.04,22.91,14.27,11.83.HRMS(m / z)(ESI):calcd for C 19 H 21 N2[M+H] + 277.1699, found 277.1690.

[0066] Example 5

[0067] Preparation and characterization of 5-butyl-4-(cyclohexa-1,5-dien-1-yl)-3-methyl-1-phenyl-1H-pyrazole (3d):

[0068] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium tetrafluoroborate were added to a 10 ml three-necked bottle, and 6 ml of a mixture of dimethyl sulfoxide and water (v:v=5:1) was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 15 mA constant current at 40 degrees Celsius for 1.5 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:30) to obtain the target product 3d.

[0069] Yellow oil (61%, 53.5 mg). 1 H NMR (400MHz, Chloroform-d) δ7.52-7.49 (m, 4H), 7.47-7.41 (m, 2H), 7.37-7.29 (m, 4H), 2.72 -2.67 (m, 2H), 2.28 (s, 3H), 1.60-1.55 (m, 2H), 1.33 (d, J = 7.5Hz, 2H), 0.85 (t, J = 7.2Hz, 3H). 13 CNMR (101MHz, Chloroform-d) δ151.53, 140.00, 136.32, 133.96, 129.74, 129.06, 128.44, 1 27.35, 126.50, 125.00, 120.68, 31.66, 26.63, 22.69, 13.87, 11.70.HRMS(m / z)(ESI):calcd for C 20 H 22 N2[M+H] + 290.1783, found 290.1778.

[0070] Example 6

[0071] Preparation and characterization of 3-methyl-1,4,5-triphenyl-1H-pyrazole (3e):

[0072] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked bottle, and 6 ml of dimethyl sulfoxide was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 20 mA constant current and 40 degrees Celsius for 3 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:35) to obtain the target product 3e.

[0073] Yellow oil(65%, 60.5mg).1H NMR (400MHz, Chloroform-d) δ7.61-7.58(m, 2H), 7.54-7.49(m, 4H), 7.43-7.36(m, 3H), 7. 34-7.31(m, 1H), 7.30-7.28(m, 1H), 7.27-7.26(m, 2H), 7.26-7.24(m, 2H), 2.32(s, 3H).13C NMR (126MHz, Chloroform-d) δ149.81, 140.05, 137.81, 133.99, 133.39, 130.47, 129.28, 128.61, 128.27, 127.87, 127.61, 126.89, 125.29, 120.25, 11.85.HRMS(m / z)(ESI):calcd for C22H19N2[M+H]+311.1543, found 311.1549.

[0074] Example 7

[0075] Preparation and characterization of 3-methyl-1,4-diphenyl-5-(p-tolyl)-1H-pyrazole (3f):

[0076] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked flask, and 6 ml of a mixture of dimethyl sulfoxide and water (v:v=5:1) was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 20 mA constant current at 35 degrees Celsius for 2.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:35) to obtain the target product 3f.

[0077] Yellow oil(66%, 64.2mg).1H NMR (400MHz, Chloroform-d) δ7.60-7.58(m, 2H), 7.52-7.48(m, 2H), 7.40-7.36(m, 5H), 7.34-7.30(m,1H),7.29-2.27(m,2H),7.08-7.06(m,2H),2.32(s,3H),2.31(s,3H).13C NMR (101MHz, Chloroform-d) δ149.82, 140.09, 137.71, 137.29, 134.14, 130.48, 129.25, 128 .99, 128.58, 128.13, 127.78, 126.83, 125.28, 120.11, 21.39, 11.84.HRMS(m / z)(ESI):calcd for C23H21N2[M+H]+325.1699, found 325.1670.

[0078] Example 8

[0079] Preparation and characterization of 5-(4-methoxyphenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3 g):

[0080] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked bottle, 6 ml of dimethyl sulfoxide was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 20 mA constant current at 15 degrees Celsius for 2.5 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:35) to obtain 3 g of the target product.

[0081] Yellow oil(65%, 66.4mg).1H NMR (400MHz, Chloroform-d) δ7.60-7.57(m, 2H), 7.52-7.48(m, 2H), 7.45-7.42(m, 2H), 7.41-7.3 7(m, 3H), 7.33-7.31(m, 1H), 7.29-7.27(m, 2H), 6.81-6.78(m, 2H), 3.78(s, 3H), 2.30(s, 3H).13C NMR (101MHz, Chloroform-d) δ159.23, 149.58, 140.10, 137.69, 134.15, 130.49, 129.48, 129.25, 128.60, 127.76, 126.83, 125.99, 125.25, 119.91, 113.71, 55.31, 11.86.HRMS(m / z)(ESI):calcd for C23H21N2O[M+H]+341.1648, found341.1658.

[0082] Example 9

[0083] Preparation and characterization of 5-(4-fluorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3h):

[0084] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, 6 ml of acetonitrile was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 10 mA constant current at 25 degrees Celsius for 3 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether = 1:30) to obtain the target product 3h.

[0085] Yellow oil(67%, 66.0mg).1H NMR (400MHz, Chloroform-d) δ7.58-7.56(m, 2H), 7.52-7.45(m, 4H), 7.42-7.35( m, 3H), 7.33-7.30 (m, 1H), 7.26-7.24 (m, 2H), 6.96-6.91 (m, 2H), 2.30 (s, 3H).13C NMR (101MHz, Chloroform-d) δ 162.52 (d, J = 244.8Hz, 1JCF), 148.91, 139.96, 137.88, 133.79, 130.41, 129.92 (d, J = 8.0Hz, 3JCF), 129.53 (d, J = 3.1Hz, 4JCF) ), 129.30, 128.69, 127.93, 127.01, 125.24, 120.09, 115.21 (d, J=21.4Hz, 2JCF), 11.81.19FNMR (376MHz, Chloroform-d) δ-114.64.HRMS (m / z) (ESI):calcd for C22H18FN2[M+H]+329.1449, found 329.1456.

[0086] Example 10

[0087] Preparation and characterization of 5-(4-chlorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3i):

[0088] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium tetrafluoroborate were added to a 10 ml three-necked bottle, and 6 ml of dimethyl sulfoxide was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 12 mA constant current at 20 degrees Celsius for 0.5-3 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:30) to obtain the target product 3i.

[0089] Yellow oil(69%, 71.4mg).1H NMR (400MHz, Chloroform-d) δ7.60-7.56(m, 2H), 7.54-7.49(m, 2H), 7.46-7.37( m, 5H), 7.37-7.33 (m, 1H), 7.28-7.24 (m, 2H), 7.24-7.21 (m, 2H), 2.30 (s, 3H).13C NMR (101MHz, Chloroform-d) δ148.64, 139.93, 138.02, 133.69, 133.45, 131.94, 130.40, 129. 47, 129.33, 128.74, 128.49, 128.01, 127.10, 125.26, 120.25, 11.79.HRMS(m / z)(ESI):calcd for C22H18ClN2[M+H]+345.1153, found 345.1155.

[0090] Embodiment 11

[0091] Preparation and characterization of 5-(3-bromo-4-fluorophenyl)-3-methyl-1,4-diphenyl-1H-pyrazole (3j):

[0092] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium tetrafluoroborate were added to a 10 ml three-necked bottle, 6 ml of acetonitrile was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 16 mA constant current at 25 degrees Celsius for 3 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:40) to obtain the target product 3j.

[0093] Yellow oil(61%, 74.5mg).1H NMR (400MHz, Chloroform-d) δ7.84-7.81(m, 1H), 7.58-7.49(m, 4H), 7.44-7.34(m, 4H), 7.30-7.27(m, 1H), 7.27-7.23(m, 2H), 6.95(t, J=8.4Hz, 1H), 2.30(s, 3H).13C NMR (101MHz, Chloroform-d) δ158.64 (d, J=246.2Hz, 1JCF), 147.50, 139.82, 138.13, 133.37, 133.03, 131.10 (d, J=3.8Hz, 4JCF), 130.36, 129 .36, 128.82, 128.73 (d, J=7.1Hz, 3JCF), 128.13, 127.28, 125.26, 120.23, 116.11 (d, J=22.3Hz, 2JCF), 108.97 (d, J=20.8Hz, 2JCF), 11.74.19F NMR(376MHz, Chloroform-d)δ-109.16.HRMS(m / z)(ESI):calcd for C22H17BrFN2[M+H]+407.0554, found 407.0550.

[0094] Example 12

[0095] Preparation and characterization of 5-(5-bromofuran-2-yl)-3-methyl-1,4-diphenyl-1H-pyrazole (3k):

[0096] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked bottle, and 6 ml of acetonitrile was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 5 mA constant current at 40 degrees Celsius for 3 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether = 1:30) to obtain the target product 3k.

[0097] Yellow oil(63%, 71.7mg).1H NMR (400MHz, Chloroform-d) δ7.56-7.48 (m, 4H), 7.44-7.41 (m, 3H), 7.39-7.34 (m, 3H), 6.22 (d, J=3.2Hz, 1H), 6.09 (d, J=3.2Hz, 1H), 2.24 (s, 3H).13C NMR (101MHz, Chloroform-d) δ150.14, 140.92, 139.72, 137.98, 132.98, 130.48, 129.29, 128. 65, 128.21, 127.56, 125.50, 121.68, 119.70, 112.80, 110.54, 11.47.HRMS(m / z)(ESI):calcd for C20H16BrN2O[M+H]+378.0368, found 378.0378.

[0098] Embodiment 13

[0099] Preparation and characterization of 5-(4-bromothiophen-2-yl)-3-methyl-1,4-diphenyl-1H-pyrazole (3l):

[0100] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acetic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked bottle, and 6 ml of dimethyl sulfoxide was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 7 mA constant current at 35 degrees Celsius for 2.5 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether = 1:40) to obtain the target product 3l.

[0101] Yellow oil(55%, 65.2mg).1H NMR (600MHz, Chloroform-d) δ7.56-7.54(m, 2H), 7.52-7.50(m, 2H), 7.47-7.44(m, 2H), 7.43- 7.39 (m, 2H), 7.36-7.34 (m, 2H), 7.06 (d, J=1.2Hz, 1H), 6.83 (d, J=0.8Hz, 1H), 2.24 (s, 3H).13 CNMR (101MHz, Chloroform-d) δ143.51, 139.67, 138.38, 137.38, 132.89, 130.65, 129.34, 128 .84, 128.15, 127.79, 127.41, 125.26, 122.06, 120.05, 109.70, 11.59.HRMS(m / z)(ESI):calcd for C20H15BrN2NaS[M+Na]+417.0032, found417.0040.

[0102] Embodiment 14

[0103] Preparation and characterization of methyl-5-(naphthalen-2-yl)-1,4-diphenyl-1H-pyrazole (3m):

[0104] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetraethylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, 6 ml of acetonitrile was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 9 mA constant current at 35 degrees Celsius for 2.5 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:30) to obtain the target product 3m.

[0105] Yellow oil(62%, 67.0mg).1H NMR (400MHz, Chloroform-d) δ8.02-8.01(m, 1H), 7.79-7.77(m, 1H), 7.74-7.69(m, 2H), 7.65-7.62( m, 3H), 7.56-7.51 (m, 2H), 7.45-7.40 (m, 3H), 7.40-7.36 (m, 2H), 7.37-7.31 (m, 3H), 2.35 (s, 3H).13C NMR (101MHz, Chloroform-d) δ149.69, 140.06, 137.95, 133.98, 133.47, 132.91, 130.92, 130.51, 129.32, 128.65, 128.42, 127.94, 127.69, 127.10, 126.98, 126.46, 125.94, 125.92, 125.34, 120.49, 11.84.HRMS(m / z)(ESI):calcd for C26H21N2[M+H]+361.1699, found 361.1697.

[0106] Embodiment 15

[0107] Preparation and characterization of 3-ethyl-5-methyl-1,4-di-p-tolyl-1H-pyrazole (3n):

[0108] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetraethylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, and 6 ml of acetonitrile was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 17 mA constant current and 10 degrees Celsius for 3 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:20) to obtain the target product 3n.

[0109] Yellow oil (75%, 65.3mg).1H NMR (400MHz, Chloroform-d) δ7.36-7.33 (m, 2H), 7.28-7.25 (m 3H), 7.23-7.19 (m, 3H), 2.68 (q, J=7.6Hz, 2H), 2.41 (d, J=4.8Hz, 6H), 2.28 (s, 3H), 0.90 (t, J=7.6Hz, 3H).13C NMR (101MHz, Chloroform-d) δ147.05, 142.51, 137.90, 137.76, 136.27, 131.12, 129.81, 12 9.70, 129.30, 125.67, 119.98, 21.35, 21.30, 18.16, 13.90, 12.58.HRMS(m / z)(ESI):calcd for C20H23N2[M+H]+291.1856, found 291.1857.

[0110] Example 16

[0111] Preparation and characterization of 1,4-bis(4-(tert-butyl)phenyl)-3-ethyl-5-methyl-1H-pyrazole (3o):

[0112] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, and 6 ml of dimethyl sulfoxide was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 20 mA constant current and 20 degrees Celsius for 2.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether = 1:25) to obtain the target product 3o.

[0113] Yellow oil(71%, 79.8mg).1H NMR (500MHz, Chloroform-d) δ7.50-7.47(m, 2H), 7.47-7.43(m, 2H), 7.41-7.38(m, 2H), 7.28-7.2 5 (m, 2H), 2.73 (q, J=7.5Hz, 2H), 2.31 (s, 3H), 1.38 (s, 9H), 1.37 (s, 9H), 0.95 (t, J=7.5Hz, 3H).13C NMR (126MHz, Chloroform-d) δ151.05, 149.31, 147.08, 142.51, 137.69, 131.08, 129.34, 126.12, 1 25.42, 125.37, 119.87, 34.82, 34.66, 31.55, 31.49, 18.18, 14.06, 12.69.HRMS(m / z)(ESI):calcd for C26H34N2Na[M+Na]+397.2614, found 397.2621.

[0114] Embodiment 17

[0115] Preparation and characterization of 1,4-bis(4-chlorophenyl)-3-ethyl-5-methyl-1H-pyrazole (3p):

[0116] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetrabutylammonium tetrafluoroborate were added to a 10 ml three-necked bottle, and 6 ml of a mixture of dimethyl sulfoxide and water (v:v=5:1) was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 20 mA constant current at 25 degrees Celsius for 0.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:20) to obtain the target product 3p.

[0117] Yellow oil(67%, 66.6mg).1H NMR (500MHz, Chloroform-d) δ7.50-7.47 (m, 2H), 7.45-7.42 (m, 4H), 7.30-7.25 (m, 2H), 2.71 (q, J=7.5Hz, 2H), 2.28 (s, 3H), 0.94 (t, J=7.5Hz, 3H).13C NMR (126MHz, Chloroform-d) δ147.60, 142.62, 138.66, 133.85, 132.85, 132.32, 131 .06, 129.50, 128.88, 126.85, 119.61, 18.14, 13.81, 12.49.HRMS(m / z)(ESI):calcd for C18H17Cl2N2[M+H]+331.0763found 331.0770.

[0118] Embodiment 18

[0119] Preparation and characterization of 3-ethyl-5-methyl-1,4-bis(4-(trifluoromethyl)phenyl)-1H-pyrazole (3q):

[0120] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetrabutylammonium iodide were added to a 10 ml three-necked bottle, and 6 ml of dimethyl sulfoxide was added to dissolve. A carbon rod was used as an anode and a platinum sheet was used as a cathode. The reaction was stirred at 15 mA constant current at 40 degrees Celsius for 0.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:15) to obtain the target product 3q.

[0121] Yellow oil(65%,77.7mg).1H NMR (400MHz, Chloroform-d) δ7.77-7.75(m, 2H), 7.71-7.69(m, 2H), 7.64-7.62(m, 2 H), 7.44-7.42 (m, 2H), 2.76 (q, J=7.6Hz, 2H), 2.29 (s, 3H), 0.93 (t, J=7.6Hz, 3H).13C NMR (126MHz, Chloroform-d) δ148.20, 142.91, 137.55, 130.03, 130.01 (d, J=32.7Hz, 2JCF), 129.18 (d, J=32.2Hz, 2JCF), 126.62 (d, J=3.8Hz, 3JCF), 125.68 (d, J=3.9Hz, 3JCF), 125.49, 123.95 (d, J=271.0Hz, 1JCF), 123.32, 120.19, 18.25, 13.83, 12.55.19F NMR(376MHz, Chloroform-d)δ-62.43,-62.46.HRMS(m / z)(ESI):calcd for C20H17F6N2[M+H]+399.1290found 399.1297.

[0122] Embodiment 19

[0123] Preparation and characterization of methyl 4-(5-ethyl-1-(4-(2-methoxy-2-oxoethyl)phenyl)-3-methyl-1H-pyrazol-4-yl)benzoate (3r):

[0124] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoromethanesulfonic acid, and 0.3 mmol of tetrabutylammonium tetrafluoroborate were added to a 10 ml three-necked bottle, 6 ml of acetonitrile was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 25 mA constant current at 40 degrees Celsius for 3 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:20) to obtain the target product 3r.

[0125] Yellow oil(62%, 73.0mg).1H NMR (400MHz, Chloroform-d) δ8.18-7.15 (m, 2H), 8.12-8.09 (m, 2H), 7.58-7.56 (m, 2H), 7.40-7. 37 (m, 2H), 3.95 (d, J=2.8Hz, 6H), 2.78 (q, J=7.2Hz, 2H), 2.29 (s, 3H), 0.91 (t, J=7.6Hz, 3H).13C NMR (101MHz, Chloroform-d) δ167.11, 166.45, 148.13, 143.760, 142.82, 138.71, 130.86, 129.97, 1 29.65, 129.37, 128.61, 124.90, 120.49, 52.48, 52.30, 18.32, 13.70, 12.64.HRMS(m / z)(ESI):calcd forC23H24N2NaO4[M+Na]+415.1628found 415.1619.

[0126] Embodiment 20

[0127] Preparation and characterization of 5-ethyl-3-methyl-1,4-di(naphthalen-2-yl)-1H-pyrazole (3s):

[0128] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphate were added to a 10 ml three-necked bottle, 6 ml of acetonitrile was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 20 mA constant current at 35 degrees Celsius for 0.5 hours. The reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:35) to obtain the target product 3s.

[0129] Yellow oil(60%, 65.2mg).1H NMR (400MHz, Chloroform-d) δ7.80-7.97(m, 2H), 7.94-7.87(m, 5H), 7.82-7.80(m, 1H), 7.67-7.64(m, 1H), 7 .57-7.49 (m, 5H), 2.85 (q, J=7.6Hz, 2H), 2.38 (s, 3H), 0.94 (t, J=7.2Hz, 3H).13CNMR (101MHz, Chloroform-d )δ147.68, 143.27, 133.69, 133.44, 132.73, 132.37, 129.38, 128.48, 128.24, 128.34, 128.21, 127.99, 127. 87, 127.01, 126.76, 126.37, 126.00, 124.06, 124.00, 120.56, 18.40, 13.94, 12.65.HRMS(m / z)(ESI):calcd for C26H23N2[M+H]+363.1856found 363.1851.

[0130] Embodiment 21

[0131] Preparation and characterization of 1,4-bis(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-ethyl-3-methyl-1H-pyrazole (3t):

[0132] 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of trifluoroacetic acid, and 0.3 mmol of tetrabutylammonium hexafluorophosphonate were added to a 10 ml three-necked bottle, 6 ml of dimethyl sulfoxide was added to dissolve, a carbon rod was used as an anode, a platinum sheet was used as a cathode, and a stirring reaction was carried out at 20 mA constant current at 40 degrees Celsius for 3 hours. The reaction process was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (3×5 ml). The organic layer was dried over anhydrous sodium sulfate, the solvent was dried under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / petroleum ether=1:15) to obtain the target product 3t.

[0133] Yellow oil(52%, 90.4mg).1H NMR (400MHz, Chloroform-d) δ7.52 (d, J=2.4Hz, 1H), 7.41-7.32 (m, 4H), 7.32-7.26 (m, 2H), 7.25-7.20 (m, 4H), 7.13-7. 10 (m, 1H), 7.06-6.99 (m, 5H), 5.20 (s, 2H), 5.19 (s, 2H), 2.64 (q, J=7.6Hz, 2H), 2.25 (s, 3H), 0.93 (t, J=7.2Hz, 3H).13C NMR (101MHz, Chloroform-d) δ163.17 (d, J=245.5Hz, 1JCF), 154.14, 153.13, 147.25, 143.42, 139.22, 139.14, 138.68, 13 8.60, 132.86, 131.59, 130.43 (d, J=8.2Hz, 2JCF), 130.37 (d, J=8.0Hz, 2JCF), 129.10, 128.25, 127.16, 125.40, 123.85, 12 3.43, 122.58, 122.55, 122.51, 118.90, 115.25 (d, J=20.9Hz, 3JCF), 115.10 (d, J=20.9Hz, 3JCF), 114.23, 114.08, 114.01 ,113.86,70.41,70.23,18.02,13.82,12.08.19FNMR(376MHz,Chloroform-d)δ-112.42,-112.55.HRMS(m / z)(ESI):calcd forC32H27Cl2F2N2O2[M+H]+579.1412found 579.1417.

[0134] The above disclosure is only a preferred embodiment of the synthesis method of a polysubstituted pyrazole compound of the present invention, and it is certainly not used to limit the scope of the present invention. A person skilled in the art can understand that all or part of the processes of the above embodiment and equivalent changes made according to the claims of the present invention still fall within the scope of the invention.

Claims

1. A method for synthesizing a polysubstituted pyrazole compound, characterized in that: The steps include: 0.6 mmol of aryl diazonium salt, 0.9 mmol of enone, 0.5 ml of acid and 0.3 mmol of electrolyte were added to a 10 ml three-necked flask, and 6 ml of solvent was added thereto to dissolve; A carbon rod was used as an anode and a platinum sheet was used as a cathode to carry out a stirring reaction, and the reaction progress was monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate; The organic layer of the mixture is dried over anhydrous sodium sulfate, the solvent is evaporated under reduced pressure, and the residue is purified by column chromatography to obtain the target product.

2. The method for synthesizing a polysubstituted pyrazole compound according to claim 1, characterized in that ； The acid includes one or more of acetic acid, trifluoromethanesulfonic acid and trifluoroacetic acid.

3. The method for synthesizing a polysubstituted pyrazole compound according to claim 1, characterized in that ； The electrolyte includes one or more of tetrabutylammonium hexafluorophosphonate, tetraethylammonium hexafluorophosphonate, tetrabutylammonium tetrafluoroborate and tetrabutylammonium iodide.

4. The method for synthesizing a polysubstituted pyrazole compound according to claim 1, characterized in that ； The solvent includes acetonitrile, dimethyl sulfoxide, and a mixture of dimethyl sulfoxide and water.

5. The method for synthesizing a polysubstituted pyrazole compound according to claim 1, characterized in that: The stirring reaction conditions include a constant current of 5-20 mA, a reaction temperature of 10-40 degrees Celsius, and a stirring reaction time of 0.5-3 hours.

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