A method for preparing an alkenyl triazole compound

Abstract

This invention discloses a method for preparing alkenyl triazole compounds. Under the action of a base, alkynyl sulfonium salts and triazole compounds are reacted in an organic solvent at room temperature and pressure for 2–5 h to obtain alkenyl triazole compounds. This invention utilizes a diamine reaction at room temperature, requiring no additional catalyst or oxidant, exhibiting excellent functional group tolerance and broad substrate applicability, while also demonstrating good chemoselectivity, regioselectivity, and stereoselectivity. The reaction system is free of toxic metal catalysts, simple to operate, and demonstrates excellent functional group tolerance and broad substrate applicability. The raw materials used are inexpensive and readily available, exhibiting good atom economy and step economy, providing a new strategy for the synthesis of triazole series compounds. The entire reaction process is mild, with high product selectivity, simple operation, and environmental friendliness, conforming to the principles of green chemistry.

Description

Technical Field

[0001] This invention relates to a method for preparing alkenyl triazole compounds, belonging to the field of organic synthesis technology. Background Technology

[0002] 1,2-Diamine motifs are common in pharmaceuticals, natural products, and functional materials. Particularly in medicinal chemistry, their chelating ability enhances the bioactivity of antibacterial and antitumor drugs. Furthermore, 1,2-diamines are frequently used as versatile bidentate nitrogen ligand building blocks, widely applied in transition metal catalysis, including cross-coupling, asymmetric hydrogenation, and C–C bond formation, enabling the efficient acquisition of structurally useful molecules (Bariwal, J.; Van der Eycken, E.). Chem. Soc. Rev. 2013, 42 , 9283−9303; Foubelo, F.; Nájera, C.; Retamosa, MG; Sansano, JM; Yus, M. Chem. Soc. Rev. 2024, 53 (e.g., 7983−8085). Therefore, the development of CN bond formation reactions has long been a research focus in the field of organic synthesis. In the past few decades, methods for constructing 1,2-diamine motifs have been developed, among which the defunctionalization of direct dienes has attracted much attention due to its step economy and high atomic efficiency. However, unlike the mature amination of alkenes and simple amines, general and highly selective strategies for direct diamineization remain scarce.

[0003] Alkyne amination is a highly efficient and atom-economical method for amination of olefins, but it has been mainly limited to monoamine amination. Recently, Tonks and colleagues reported titanium-catalyzed diamine amination of 1-phenyl-1-propene (Karmakar, PS; Kakiuchi, Y.; Kim, J.; Harris, MR; Huh, DN; Sell, AG; Copéret, C.; Tonks, IA). J. Am. Chem. Soc. 2025, 147 (11019–11027). In such reactions, most existing monoamine or diamineation methods rely on toxic metal catalysts and suffer from limited substrate range, regioselectivity and chemoselectivity issues, as well as overfunctionalization.

[0004] Patent search results, such as CN201810356998.7, disclose a one-pot method for synthesizing the target alkenyl triazole compound in a polar solvent, using 3,4,5-tris(4-bromophenyl)-1 H-1,2,4-triazole reacts with 1,2,4-triazole under the catalysis of potassium carbonate and copper oxide. The molar ratio, temperature and time parameters are optimized to improve the yield and purity. At the same time, a single crystal structure is obtained by recrystallization, which facilitates the structure confirmation and application development. However, the reaction temperature is high and the reaction time is long.

[0005] No metal-free direct diamineization method for alkyne bonds has been reported in the literature to date. Summary of the Invention

[0006] In view of the aforementioned problems in the prior art, this application presents a method for preparing alkenyl triazole compounds. Under ambient temperature and pressure, this method uses alkynyl sulfonium salts and aryl triazoles as raw materials, and efficiently and selectively introduces triazole functional groups to both ends of an alkyne via a diamine reaction, thereby obtaining the target alkenyl triazole compound. This method avoids the use of toxic metal catalysts, exhibits excellent functional group tolerance and substrate universality, and also possesses high chemoselectivity, regioselectivity, and stereoselectivity. The reaction process is simple and the conditions are mild, providing a new route for the green synthesis of related compounds.

[0007] The purpose of this invention is to solve the above-mentioned problems in the prior art and provide a method for preparing alkenyl triazole compounds. Under the action of an alkali, alkyne sulfonium salts and triazole compounds are reacted in an organic solvent at room temperature and pressure for 2-5 hours to obtain alkenyl triazole compounds, the structural formula of which is shown in the reaction equation.

[0008] Where, R 1 It is a halogen, a substituted aryl or alkyl group; R 2 It is H, a substituted aryl group, or a halogen; R 3 It is a substituted aryl group, R 1 R 2 R 3 They can be the same or different.

[0009] Preferably, the molar ratio of the triazole to the alkynyl sulfonium salt is 2:1.

[0010] Preferably, the molar ratio of the alkynyl sulfonium salt to cesium carbonate is 1:1.3.

[0011] Preferably, the alkali is cesium carbonate.

[0012] Preferably, the organic solvent is tetrahydrofuran, dioxane, ethyl acetate, benzene, toluene, dimethyl sulfoxide, acetonitrile, hexafluoroisopropanol, dichloromethane, or 1,2-dichloroethane. N , N- Dimethylformamide, acetone, methanol, ethanol, isopropanol, or any one or more of these. The structural formula of the triazole is: ; The structural formula of the alkynyl sulfonium salt is as follows: ; where R 1 It is a halogen, a substituted aryl or alkyl group; R 2 It is H, a substituted aryl group, or a halogen; R 3 It is a substituted aryl group.

[0013] Preferably, the optionally substituted aryl group is any one or more of phenyl, substituted phenyl, furan, and thiophene; the alkyl group is a C1-C4 alkyl group; wherein the substituent in the substituted phenyl group is any one or more of methyl, ethyl, halogen, methoxy, and cyano.

[0014] Preferably, the C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0015] Preferably, the alkenyltriazole compound includes the following compounds: .

[0016] The advantages of this invention over the prior art are as follows: 1. This method is an efficient synthesis method for alkenyl triazole compounds. Using alkynyl sulfonium salt and triazole as raw materials, a diamine reaction is carried out under ambient temperature and pressure conditions. It can achieve high chemoselectivity, high regioselectivity and high stereoselectivity. Triazole functional groups are introduced at both ends of the alkyne to construct novel alkenyl triazole compounds in one step. 2. The reaction system does not require the use of toxic metal catalysts, is easy to operate, has mild conditions, and exhibits excellent functional group tolerance and broad substrate applicability. 3. This synthetic strategy can be applied to the late-stage functional group modification of drug molecules, providing a new tool for the structural derivation and functional optimization of complex active molecules; 4. It significantly expands the chemical space and structural diversity of triazole derivatives, and has good application potential in the fields of medicinal chemistry, materials science and related functional molecule research and development. Attached Figure Description

[0017] Figure 1 This is the 1H NMR spectrum of product 3a prepared in Example 2 of this invention; Figure 2 This is the 1H NMR spectrum of product 3t prepared in Example 21 of this invention; Detailed Implementation

[0018] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are some embodiments of the present invention, but not all embodiments.

[0019] Unless otherwise specified, all methods used in this invention are conventional techniques in the art, all solvents are purified and dried using standard procedures before use, and all reagents are commercially available or synthesized according to existing literature methods and are purified before use.

[0020] The following examples use abbreviations for compounds, the meanings of which are as follows: Me stands for methyl, and Et stands for ethyl. n Bu is n-butyl, Ph is phenyl t Bu is tert-butyl, THF is tetrahydrofuran, PE is petroleum ether, EA is ethyl acetate, DCM is dichloromethane, NMR is nuclear magnetic resonance, and HRMS is high-resolution mass spectrometry. Example

[0021] Alkenyl triazole compounds were prepared using alkynyl sulfonium salts and triazoles as raw materials. Under air atmosphere, triazole (0.4 mmol, 2.0 equiv), alkynyl sulfonium salt 2 (0.2 mmol, 1.0 equiv), and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction was complete, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the target product 3.

[0022] The chemical equation for the reaction is as follows:

[0023] The reaction principles and chemical equations of Examples 2-21 are the same as those of Example 1, except that the specific reactants, reaction conditions and products in each example are different. Example

[0024] A sort of( Z )-2,2'-(1-phenylene-1,2-diacyl)bis(4-phenyl-2 HThe preparation method of (-1,2,3-triazole) (3a) includes the following steps:

[0025] Weigh out 0.4 mmol of 4-phenyl-1,2,3-triazole (2.0 equiv) and 5-(phenylethynyl)-5-triazole in air atmosphere. H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a white solid (…). Z )-2,2'-(1-phenylvinyl-1,2-diyl)bis(4-phenyl-2) H (-1,2,3-triazole) (3a) 46.8 mg, the yield of this product is 60%, melting point is 121.6~122.4 mg. o C; The detection data of the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3a are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.16 (s, 1H), 7.92 (s, 1H), 7.86 (s, 3H), 7.57 (s, 2H), 7.47–7.32 (m, 8H), 7.28 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 149.3, 149.3, 134.2, 133.5, 133.0, 130.1, 129.9, 129.8,129.2, 129.1, 129.1, 129.0, 128.9, 128.8, 126.3, 126.2, 126.1, 123.1. HRMS(APCI) m / z: [M+H] + Calcd for C 24 H 19 N6 391.1666; Found: 391.1668. Example

[0026] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)-(4-(4-fluorobenzene)-2 H The preparation method of (-1,2,3-triazole) (3b) includes the following steps:

[0027] Weigh out 5-(4-fluorophenyl)-1 under air atmosphere. H -1,2,3-triazole, (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-Phenylacetyl-1,2-diyl)bis(4-(4-fluorophenyl)-2 H (-1,2,3-triazole) (3b) 63.9 mg, the yield of this product was 75%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3b are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.12 (s, 1H), 7.91 (s, 1H), 7.84 (m, 3H), 7.54 (t, J = 6.6Hz, 2H), 7.46 – 7.41 (m, 3H),7.36 (m, 2H), 7.14 (t, J = 8.4 Hz, 2H), 7.00 (t, J = 8.4 Hz, 2H). 13 C NMR (151MHz, CDCl3) δ 164.1 (d, J = 15.1 Hz), 162.5 (d, J= 13.6 Hz), 148.6, 148.5,134.1, 133.3, 132.7, 130.1, 130.0, 129.2, 128.1 (d, J = 15.1 Hz), 128.0 (d, J = 13.6 Hz), 126.4 (d, J = 3.0 Hz), 126.2, 125.5 (d, J = 3.0 Hz), 123.0, 116.2 (d, J = 21.1 Hz), 116.0 (d, J = 21.1 Hz). 19 F NMR (565 MHz, CDCl3) δ -111.59, -112.32.HRMS (APCI) m / z: [M+H] + Calcd for C 24 H 17 F2N6 427.1477; Found: 427.1478. Example

[0028] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)-(4-(4-chlorophenyl)-2 H The preparation method of (-1,2,3-triazole) (3c) includes the following steps:

[0029] Weigh out 4-(4-chlorophenyl)-1- H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b,d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z)-2,2'-(1-phenylene-1,2-diyl)-(4-(4-chlorophenyl)-2 H (-1,2,3-triazole) (3c) 61.4 mg, the yield of this product was 67%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3c are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.13 (s, 1H), 7.91 (s,1H), 7.86 (s, 1H), 7.79 (d, J = 7.8Hz, 2H), 7.49 (d, J = 8.4Hz, 2H), 7.42 (d, J = 7.2 Hz, 5H), 7.36 (s, 2H), 7.28 (d, J = 8.4Hz, 2H). 13 C NMR (151 MHz, CDCl3) δ 148.3, 148.3, 135.1, 134.8, 133.9, 133.3, 132.7, 130.1, 129.9,129.2, 129.2, 129.1, 128.5, 127.6, 127.5, 127.3, 126.1, 122.9. HRMS (APCI) m / z: [M+H] + Calcd for C 24 H 17 Cl2N6 459.0886; Found:459.0890. Example

[0030] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(4-bromophenyl)-2 H The preparation method of (-1,2,3-triazole) (3d) includes the following steps:

[0031] Weigh out 4-(4-bromophenyl)-1- H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b, dThiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow solid (…). Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(4-bromophenyl)-2 H (-1,2,3-triazole) (3d) 80.7 mg, the yield of this product is 74%, melting point is 127.5~128.8 o C; The detection data of the mass spectrometry and nuclear magnetic resonance spectra of the obtained product at 3d are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.13(s, 1H), 7.90 (s, 1H), 7.86 (s, 1H), 7.72 (d, J = 7.8Hz, 2H), 7.58 (d, J =8.4Hz, 2H), 7.44 (d, J = 5.4Hz, 7H), 7.35 (dd, J = 5.4, 1.8Hz, 2H). 13 C NMR(151 MHz, CDCl3) δ 148.5, 148.4, 134.0, 133.4, 132.8, 132.3, 132.2, 130.3,130.1, 129.2, 129.1, 128.2, 127.8, 127.7, 126.3, 123.4, 123.1, 123.0.HRMS(APCI) m / z: [M+H] + Calcd for C 24 H 17 Br2N6 546.9876; Found: 546.9877. Example

[0032] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)-(4-(p-styrene)-2 HThe preparation method of (-1,2,3-triazole) (3e) includes the following steps:

[0033] Weigh out 0.4 mmol of 4-(4-methylphenyl)-1,2,3-triazole (2.0 equiv) and 5-(phenylethynyl)-5-triazole in air atmosphere. H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow solid (…). Z )-2,2'-(1-phenylene-1,2-diyl)-(4-(p-styrene)-2 H (-1,2,3-triazole) (3e) 72.7 mg, the yield of this product is 87%, melting point is 127.5~127.9 o C; The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3e are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.12(s, 1H), 7.91 (s, 1H), 7.84 (s, 1H), 7.75 (d, J = 7.8 Hz, 2H), 7.47 (d, J =7.8Hz, 2H), 7.43–7.39 (m, 3H), 7.35 (dd, J = 7.8, 3.6Hz, 2H), 7.25 (d, J =7.2Hz, 2H), 7.11 (d, J = 7.8 Hz, 2H), 2.39 (s, 3H), 2.33 (s, 3H). 13C NMR (151MHz, CDCl3) δ 149.4, 149.3, 139.1, 138.7, 134.3, 133.3, 132.6, 129.6, 129.6,129.0, 127.3, 126.4, 126.2, 126.1, 123.0, 21.4, 21.4.HRMS (APCI) m / z: [M+H] + Calcd for C 22 H 23 N6 419.1979; Found:419.1982. Example

[0034] A sort of( Z )-4,4'-((1-phenylene-1,2-diacyl)bis(2 H The preparation method of 1,2,3-triazol-2,4-diyl))dibenzonitrile (3f) includes the following steps:

[0035] Weigh 4-(1) in air. H -1,2,3-triazol-4-yl)benzonitrile (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-4,4'-((1-phenylene-1,2-diacyl)bis(2 H -1,2,3-triazol-2,4-diyl))dibenzonitrile (3f) 55.4 mg, the yield of this product is 63%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3f are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.22 (s, 1H), 7.94 (dd, J= 144, 6.6Hz, 4H), 7.74 (d, J = 7.8Hz, 2H), 7.67 (d, J = 8.4Hz, 2H), 7.60(d, J = 8.4Hz, 2H), 7.45 (d, J = 7.2Hz, 3H), 7.35 (d, J = 5.4 Hz, 2H). 13 C NMR(151 MHz, CDCl3) δ 147.5, 147.5, 134.2, 133.9, 133.4, 133.4, 133.3, 132.9,132.8, 130.8, 130.3, 129.2, 126.6, 126.5, 126.2, 122.8, 118.5, 118.4, 112.7,112.5.HRMS (APCI) m / z: [M+H] + Calcd for C 26 H 17 N8 441.1571; Found: 441.1573. Example

[0036] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4,5-diphenyl-2) H The preparation method of (-1,2,3-triazole) (3g) includes the following steps:

[0037] Weigh out 4,5-diphenyl-1-propionate in air. H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H Dibenzo[b,d]thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a white solid (Z )-2,2'-(1-phenylene-1,2-diyl)bis(4,5-diphenyl-2) H -1,2,3-triazole (3g) 94.3 mg, the yield of this product is 87%, melting point is 197.4~198.6 o C; The mass spectrometry and nuclear magnetic resonance spectra of the obtained product (3g) are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.99 (s, 1H),7.56 (d, J = 4.8 Hz, 4H), 7.49 (d, J = 7.2Hz, 2H), 7.43 (d, J = 7.8 Hz, 7H),7.35–7.28 (m, 8H), 7.24 (t, J = 7.8Hz, 4H). 13 C NMR (151 MHz, CDCl3) δ 146.7,146.5, 134.2, 130.9, 130.1, 129.7, 129.5, 129.2, 129.0, 128.6, 128.4, 126.1,123.3.HRMS (APCI) m / z: [M+H] + Calcd for C 36 H 27 N6 543.2292; Found: 543.2296. Example

[0038] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(2,6-dimethoxyphenyl)-2 H The preparation method of (-1,2,3-triazole) (3h) includes the following steps:

[0039] Weigh out 4-(2,6-dimethoxyphenyl)-1 under air atmosphere. H -1,2,3-triazole, (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , dThiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(2,6-dimethoxyphenyl)-2 H -1,2,3-triazole) (3h) 71.4 mg, the yield of this product is 70%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product after 3h are as follows: 1 H NMR (600 MHz, CDCl3) δ8.02 (d, J = 7.2Hz, 2H), 7.73 (s, 1H), 7.40–7.36 (m, 3H), 7.32–7.28 (m, 4H), 6.64 (s, 1H), 6.62 (d, J = 1.8Hz, 2H), 6.61 (s, 1H), 3.74 (d, J = 1.8Hz, 12H). 13 C NMR (151 MHz, CDCl3) δ 158.8, 158.8, 142.4, 141.8, 138.9, 137.6,135.3, 130.6, 130.2, 129.2, 128.9, 128.6, 126.1, 123.4, 108.9, 107.9, 104.5,104.3, 56.1, 56.1.HRMS (APCI) m / z: [M+H] + Calcd for C 28 H 27 N6O4 511.2088; Found:511.2097. Example

[0040] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-methyl-2 H The preparation method of (-1,2,3-triazole) (3i) includes the following steps:

[0041] Weigh out 5-(2,4,6-trimethylphenyl)-1 H -1,2,3-triazole, (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H Dibenzo[b,d]thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow solid ( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-methyl-2 H (-1,2,3-triazole) (3i) 73.0 mg, the yield of this product is 77%, melting point is 124.1~124.8 o C; The detection data of the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3i are as follows: 1 H NMR (600 MHz, CDCl3) δ8.02 (s, 1H), 7.76 (s, 1H), 7.57 (s, 1H), 7.46–7.41 (m, 3H), 7.35 (dd, J =7.8, 1.8Hz, 2H), 6.92 (d, J = 2.4Hz, 4H), 2.33 (d, J = 7.8Hz, 6H), 2.05 (s, 12H). 13 C NMR (151 MHz, CDCl3) δ 148.4, 147.7, 138.6, 138.3, 137.8, 137.6,137.0, 136.1, 134.7, 129.6, 129.3, 129.1, 128.4, 128.3, 126.9, 126.2, 125.9,123.5, 21.2, 20.6, 20.5.HRMS (APCI) m / z: [M+H] + Calcd for C30 H 31 N6 475.2605; Found: 475.2609. Example

[0042] A sort of( Z )-2,2'-(1-phenylen-1,2-diacyl)bis(4-(furan-2-yl)-2 H The preparation method of (-1,2,3-triazole) (3j) includes the following steps:

[0043] Weigh out 5-(2-furanyl)-1 under air atmosphere. H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-phenylen-1,2-diacyl)bis(4-(furan-2-yl)-2 H -1,2,3-triazole) (3j) 48.1 mg, the yield of this product is 65%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3j are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.09 (s, 1H), 7.89 (s, 1H), 7.80 (s, 1H), 7.52 (s, 1H), 7.45 (s, 1H), 7.42–7.39 (m, 3H), 7.31 (dd, J =6.6, 2.4Hz, 2H), 6.80 (d, J = 3.6Hz, 1H), 6.59 (d, J = 3.6Hz, 1H), 6.51 (s,1H), 6.44 (s, 1H).13 C NMR (151 MHz, CDCl3) δ 145.7, 145.0, 143.3, 142.9,141.8, 134.0, 133.4, 132.6, 129.9, 129.9, 129.1, 126.2, 123.0, 111.8, 111.7,108.7, 108.1.HRMS (APCI) m / z:[M+H] + Calcd for C 20 H 15 N6O2 371.1251; Found:371.1254. Example

[0044] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(thiophen-2-yl)-2 H The preparation method of (-1,2,3-triazole) (3k) includes the following steps:

[0045] Weigh out 5-(thiophene-2-yl)-1 under air atmosphere. H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-(thiophen-2-yl)-2 H (-1,2,3-triazole) (3k) 43.4 mg, the yield of this product was 54%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3k are as follows: 1H NMR (600 MHz, CDCl3) δ 8.06 (s, 1H), 7.89 (s, 1H),7.78 (s, 1H), 7.49 (d, J = 3.6 Hz, 1H), 7.44–7.41 (m, 3H), 7.35 (dd, J = 7.2,3.0 Hz, 3H), 7.29–7.27 (m, 2H), 7.11 (t, J = 4.8Hz, 1H), 7.01 (t, J = 4.2Hz, 1H). 13 C NMR (151 MHz, CDCl3) δ 144.8, 144.6, 134.0, 133.2, 132.8, 132.5,131.7, 129.9, 129.7, 129.1, 127.8, 127.8, 126.9, 126.2, 126.1, 125.9, 125.5,123.0.HRMS (APCI) m / z: [M+H] + Calcd for C 20 H 15 N6S2 403.0794; Found: 403.0798. Example

[0046] A sort of( Z )-4-(1,2-bis(4-phenyl-2-) H The preparation method of 1,2,3-triazol-2-yl)vinylbenzoate (3l) includes the following steps:

[0047] Weigh out 0.4 mmol of 4-phenyl-1,2,3-triazole (2.0 equiv) and 5-((4-(methoxycarbonyl)phenyl)ethynyl)-5-triazole in air atmosphere. H -dibenzo[ b , dThiophene-5-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid. Z )-4-(1,2-bis(4-phenyl-2-) H -1,2,3-triazol-2-yl)vinylbenzoate (3l) 52.0 mg, the yield of this product was 58%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3l are as follows. 1 H NMR (600 MHz, CDCl3) δ 8.19 (s, 1H), 8.08 (d, J =9.0Hz, 2H), 8.04 (s, 1H), 7.91 (s, 1H), 7.87 (d, J = 7.2Hz, 2H), 7.60–7.56(m, 2H), 7.46 (t, J = 7.2Hz, 2H), 7.43–7.38 (m, 3H), 7.31–7.29 (m, 3H), 3.94(s, 3H). 13 C NMR (151 MHz, CDCl3) δ 166.5, 149.9, 149.6, 138.6, 134.1, 133.2,131.0, 130.4, 130.1, 129.4, 129.1, 129.0, 129.0, 128.5, 126.4, 126.3, 125.9,124.7, 52.4.HRMS (APCI) m / z: [M+H] + Calcd for C 26 H 21 N6O2 449.1721; Found:449.1723. Example

[0048] A sort of( Z )-2,2'-(1-(4-chlorophenyl)vinyl-1,2-diyl)bis(4-phenyl-2) HThe preparation method of -1,2,3-triazole)(3m) includes the following steps:

[0049] Weigh out 0.4 mmol of 4-phenyl-1,2,3-triazole (2.0 equiv) and 5-((4-chlorophenyl)ethyl)-5-triazole in air atmosphere. H -dibenzo[ b , d Thiophene-5-trifluoromethane sulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid. Z )-2,2'-(1-(4-chlorophenyl)vinyl-1,2-diyl)bis(4-phenyl-2 H -1,2,3-triazole) (3m) 77.9 mg, the yield of this product was 85%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3m are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.19 (s, 1H), 7.92 (s, 1H), 7.89 – 7.88 (m, 3H), 7.59 (dd, J = 6.0, 2.4Hz, 2H), 7.46 (t, J = 7.8Hz, 2H), 7.40 (dd, J = 7.8, 5.4Hz, 3H), 7.31–7.29 (m, 5H). 13 C NMR (151 MHz, CDCl3) δ149.5, 149.5, 135.8, 133.7, 133.1, 132.8, 130.0, 129.3, 129.2, 129.1, 129.0,129.0, 128.9, 128.7, 127.4, 126.3, 126.2, 123.3.HRMS (APCI) m / z: [M+H] + Calcdfor C 24 H18 ClN6 425.1276; Found: 425.1277. Example

[0050] A sort of( Z )-2,2'-(1-(p-methyl)vinyl-1,2-diyl)bis(4-phenyl-2 H The preparation method of (-1,2,3-triazole) (3n) includes the following steps:

[0051] Weigh out 0.4 mmol of 4-phenyl-1,2,3-triazole (2.0 equiv) and 5-(p-methylphenylethynyl)-5-triazole in air atmosphere. H -dibenzo[ b , d Thiophene-5-trifluoromethane sulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid. Z )-2,2'-(1-(p-methyl)vinyl-1,2-diyl)bis(4-phenyl-2 H -1,2,3-triazole) (3n) 59.0 mg, the yield of this product was 73%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3n are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.14 (s, 1H), 7.86 (m, 4H), 7.57 (dd, J = 5.4, 3.0Hz, 2H), 7.43 (m, 2H), 7.39–7.34 (m, 1H), 7.28 (m, 3H),7.25–7.24 (m, 2H), 7.21 (d, J = 8.4Hz, 2H), 2.38 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 149.23, 149.2, 140.1, 133.4, 132.9, 131.4, 130.2, 129.8, 129.3, 129.1, 129.0, 128.9, 128.9, 126.4, 126.2, 126.2, 122.3, 21.5.HRMS (APCI) m / z:[M+H] + Calcd for C 25 H 21 N6 405.1822; Found: 405.1825. Example

[0052] A sort of( Z )-2,2'-(1-(4-(tert-butyl)phenyl)ethylene-1,2-diyl)bis(4-phenyl-2 H The preparation method of (-1,2,3-triazole) (3o) includes the following steps:

[0053] Weigh out 0.4 mmol of 4-phenyl-1,2,3-triazole (2.0 equiv) and 5-((4-(tert-butyl)phenyl)ethyl)-5-triazole in air atmosphere. H -dibenzo[ b , d Thiophene-5-trifluoromethane sulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid. Z )-2,2'-(1-(4-(tert-butyl)phenyl)ethylene-1,2-diyl)bis(4-phenyl-2 H -1,2,3-triazole) (3o) 60.7 mg, the yield of this product was 68%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3o are as follows: 1H NMR (600 MHz, CDCl3) δ 8.16 (s, 1H), 7.90 (s, 1H), 7.87–7.86 (m, 3H), 7.58 (dd, J = 6.6, 3.0 Hz, 2H), 7.44 (dt, J = 7.8, 3.6Hz, 4H), 7.38 (t, J = 7.2Hz, 1H), 7.31–7.29 (m, 5H), 1.34 (s, 9H). 13 C NMR (151 MHz, CDCl3) δ 153.3, 149.3, 133.4, 132.9, 131.3, 130.3, 130.1,129.4, 129.2, 129.0, 129.0, 128.9, 126.4, 126.3, 126.2, 126.0, 122.4, 35.0,31.3.HRMS (APCI) m / z: [M+H] + Calcd for C 28 H 27 N6 447.2292; Found: 447.2293. Example

[0054] A sort of( Z )-2,2'-(1-phenylene-1,2-diacyl)bis(4,5-dibromo-2 H The preparation method of (-1,2,3-triazole) (3p) includes the following steps:

[0055] Weigh out 4,5-dibromo-1 in air. H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , dThiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow solid (…). Z )-2,2'-(1-phenylene-1,2-diacyl)bis(4,5-dibromo-2 H -1,2,3-triazole) (3p) 85.8 mg, the yield of this product is 78%, melting point is 141.1~143.6 o C; The detection data of the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3p are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.62 (s, 1H), 7.44 (m3H), 7.31–7.27 (m, 2H). 13 C NMR (151 MHz, CDCl3) δ 132.3, 130.8, 130.7, 129.4,128.5, 127.4, 126.5, 122.3.HRMS (APCI) m / z: [M+H] + Calcd for C 12 H7Br4N6550.7460; Found: 550.7464. Example

[0056] A dimethyl 2,2'-(1-phenylene-1,2-diyl)( Z )-double(2 H The preparation method of (-1,2,3-triazole-4-carboxylate) (3q) includes the following steps:

[0057] Weigh out 0.4 mmol (2.0 equiv) of methyl 1,2,3-triazole-4-carboxylate and 5-(phenylethynyl)-5-carboxylate in air. H -dibenzo[ b , dThiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding a crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid, dimethyl 2,2'-(1-phenylene-1,2-diyl) Z )-double(2 H -1,2,3-triazole-4-carboxylate) (3q) 48.9 mg, the yield of this product was 69%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3q are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.33 (s, 1H), 7.97 (s, 1H), 7.93 (s,1H), 7.43 (dt, J = 14.4, 7.2 Hz, 3H), 7.25 (d, J = 7.8Hz, 2H), 3.98 (s, 3H), 3.93 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 161.0, 160.3, 141.7, 141.3, 138.6,138.5, 132.8, 132.2, 130.8, 129.4, 126.4, 123.2, 52.7, 52.7.HRMS (APCI) m / z:[M+H] + Calcd for C 16 H 15 N6O4 355.1149; Found: 355.1152. Example

[0058] A sort of( Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-cyclopropyl-2 H The preparation method of (-1,2,3-triazole) (3r) includes the following steps:

[0059] Weigh out 4-cyclopropyl-1-propanediol in air. H-1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-phenylene-1,2-diyl)bis(4-cyclopropyl-2 H -1,2,3-triazole) (3r) 48.3 mg, the yield of this product was 76%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3r are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.71 (s, 1H), 7.54 (s, 1H), 7.39 (s, 1H),7.37–7.36 (m, 3H), 7.23 (dd, J = 6.6, 3.0Hz, 2H), 2.03 (m, 1H), 1.80 (m, 1H), 1.03–1.00 (m, 2H), 0.93 – 0.91 (m, 2H), 0.86–0.83 (m, 2H), 0.72–0.69 (m, 2H). 13 C NMR (151 MHz, CDCl3) δ 153.0, 152.4, 134.6, 134.4, 132.8, 129.5, 129.1,129.0, 126.0, 122.9, 8.6, 8.5, 7.0, 6.7.HRMS (APCI) m / z: [M+H] + Calcd forC 18 H 19 N6 319.1666; Found: 319.1667. Example

[0060] A sort of( Z )-2,2'-(1-phenylene-1,2-diacyl)bis(4-butyl-2H The preparation method of (-1,2,3-triazole) (3S) includes the following steps:

[0061] Weigh out 5-butyl-1 in air. H -1,2,3-triazole (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid (…). Z )-2,2'-(1-phenylene-1,2-diacyl)bis(4-butyl-2 H -1,2,3-triazole)(3s) 45.1 mg, the yield of this product was 62%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3s are as follows. 1 H NMR (600 MHz, CDCl3) δ 7.76 (s, 1H), 7.62 (s, 1H), 7.37–7.35 (m, 4H), 7.22 (dd, J = 7.8, 3.6Hz, 2H), 2.76 (t, J = 7.8Hz, 2H), 2.56 (t, J = 7.8Hz, 2H), 1.69 (p, J = 7.8Hz, 2H), 1.54 (p, J = 7.8Hz, 2H), 1.41 (H, J = 7.8Hz, 2H), 1.31 (H, J = 7.8Hz, 2H), 0.94 (t, J = 7.2Hz, 3H), 0.90 (t, J = 7.2Hz, 3H). 13C NMR (151 MHz, CDCl3) δ 150.8, 150.2, 135.3, 134.6, 134.4, 129.4,129.3, 128.9, 126.0, 122.8, 31.5, 30.7, 25.3, 25.1, 22.2, 13.9, 13.8.HRMS(APCI) m / z: [M+H] + Calcd for C 20 H 27 N6 351.2292; Found:351.2293. Example

[0062] A sort of( Z ) N,N '-((1-phenylene-1,2-diyl)bis(2 H -1,2,3-triazole-2,4-diyl))bis(4,1-benzene))bis(4-( N,N The preparation method of (-dipropylsulfonyl)benzamide (3t) includes the following steps:

[0063] Weigh in air. N -(4-(1 H -1,2,3-triazol-4-yl)phenyl)-4-( N , N (-Dipropylsulfonyl)benzoyl (0.4 mmol, 2.0 equiv), 5-(phenylethynyl)-5 H -dibenzo[ b , d Thiophene-trifluoromethanesulfonate (0.2 mmol, 1.0 equiv) and cesium carbonate (0.26 mmol, 1.3 equiv) were sequentially added to a dry 10 mL pressure-resistant reaction tube. Then, dichloromethane (DCM, 5 mL) was added as a solvent, and the reaction was carried out under ambient temperature and pressure with magnetic stirring for 2 hours. After the reaction, the mixture was extracted three times with dichloromethane (5 mL × 3), the organic layers were combined, and dried over anhydrous sodium sulfate. After drying, the desiccant was filtered off, and the resulting organic phase was concentrated by rotary evaporation to remove the solvent, yielding the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain a yellow liquid. Z ) N , N '-((1-phenylene-1,2-diyl)bis(2 H-1,2,3-triazole-2,4-diyl))bis(4,1-benzyl))bis(4-(N,N-dipropylsulfonyl)benzamide) (3t) 125.9 mg, the yield of this product was 66%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 3t are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.84 (d, J = 8.4Hz, 2H), 8.15 (s, 1H),7.97–7.83 (m, 6H), 7.81–7.78 (m, 2H), 7.76–7.73 (m, 2H), 7.69–7.61 (m, 6H),7.47 (d, J = 8.4 Hz, 2H), 7.40–7.39 (m, 2H), 7.32 (m, 2H), 3.05–3.02 (m, 8H), 1.54–1.47 (m, 8H), 0.85–0.81 (m, 12H), 0.77 (t, J = 7.2Hz, 1H). 13 C NMR (151MHz, CDCl3) δ 165.1, 165.0, 148.9, 148.8, 142.8, 142.8, 138.8, 138.6, 138.6,138.5, 134.0, 133.3, 132.8, 129.8, 129.6, 129.1, 128.2, 128.2, 127.2, 127.0,126.8, 126.6, 126.0, 125.5, 125.2, 123.1, 121.2, 120.8, 50.1, 50.1, 22.0,22.0, 11.2.HRMS (APCI) m / z: [M+H] + Calcd for C 50 H 55 N 10 O6S2 955.3742; Found:955.3749. The above embodiments are merely explanations and illustrations of the technical solutions of the present invention and should not be used to limit the scope of protection of the technical solutions of the present invention. All simple modifications based on this solution are within the scope of protection of the present invention.

Claims

1. A method for preparing an alkenyl triazole compound, comprising reacting an alkynyl sulfonium salt and a triazole compound as raw materials in an organic solvent at room temperature and pressure for 2–5 hours under the action of an alkali to obtain an alkenyl triazole compound with the following structural formula: , where R 1 It is a halogen, a substituted aryl or alkyl group; R 2 It is H, a substituted aryl group, or a halogen; R 3 It is a substituted aryl group.

2. The method for preparing alkenyl triazole compounds according to claim 1, characterized in that: The structural formula of the triazole is: ； The structural formula of the alkynyl sulfonium salt is: ； Among them, R 1 It is a halogen, a substituted aryl or alkyl group; R 2 It is H, a substituted aryl group, or a halogen; R 3 It is a substituted aryl group.

3. The method for preparing alkenyl triazole compounds according to claim 2, characterized in that: The molar ratio of the triazole to the alkynyl sulfonium salt is 2:

1.

4. The method for preparing alkenyl triazole compounds according to claim 1, characterized in that: The alkali is cesium carbonate.

5. The method for preparing alkenyl triazole compounds according to claim 4, characterized in that: The molar ratio of the alkynyl sulfonium salt to cesium carbonate is 1:1.

3.

6. The method for preparing alkenyltriazole compounds according to claim 1, characterized in that: The organic solvent is tetrahydrofuran, dioxane, ethyl acetate, benzene, toluene, dimethyl sulfoxide, acetonitrile, hexafluoroisopropanol, dichloromethane, 1,2-dichloroethane. N , N - any one or more of dimethylformamide, acetone, methanol, ethanol, and isopropanol.

7. The method for preparing the alkenyltriazole compound according to claim 1 or 2, characterized in that: The substituted aryl group is any one or more of phenyl, substituted phenyl, furan, and thiophene; the alkyl group is a C1-C4 alkyl group; and the substituent in the substituted phenyl group is any one or more of methyl, ethyl, halogen, methoxy, and cyano.

8. The method for preparing alkenyl triazole compounds according to claim 7, characterized in that: The C1-C4 alkyl group is one of methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

9. The method for preparing alkenyl triazole compounds according to claim 1, characterized in that: The alkenyltriazole compounds include the following compounds: 。

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