CN109776435B - Method for preparing 1,2, 3-triazole by dibromovinylbenzene one-pot method - Google Patents
Method for preparing 1,2, 3-triazole by dibromovinylbenzene one-pot method Download PDFInfo
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Abstract
The invention discloses a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which comprises the following steps: adding a 2, 2-dibromo vinyl benzene compound, sodium azide, a nitrobenzene compound, alkali, a catalyst and sodium ascorbate into a reaction vessel containing an organic solvent; reacting under the protection of nitrogen; after the reaction is finished, carrying out post-treatment, and then carrying out recrystallization or silica gel column chromatography separation and purification to obtain the 1,2, 3-triazole compound; the catalyst is a salt of a monovalent or divalent copper. The method has the advantages of high safety, simple operation, mild condition, low cost, easy industrial production and the like.
Description
Technical Field
The invention belongs to the field of organic synthesis, relates to a method for synthesizing 1,2, 3-triazole, and particularly relates to a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method.
Background
1,2, 3-triazole and derivatives thereof, which are important parts of nitrogen-containing heterocyclic compounds, are not found in nature, and the main sources of the compounds completely depend on artificial synthesis. In 2001, Sharpless et al discovered that the transition metal copper can well catalyze the Huisgen1, 3-dipolar cycloaddition reaction of organic azide and terminal alkyne, referred to as CuACC reaction for short[1]. The reaction substrate has wide applicability, high reaction speed, high yield and good regioselectivity[2]The compound has milestone significance in the synthesis of 1,2, 3-triazole.
The 1,2, 3-triazole compound is a very important compound, has the stability of aromatic ring and good biocompatibility[3]The pharmacophores of different substrates are linked into a molecule through triazole rings, the binding capacity of the product with a biological target can be improved through hydrogen bond and dipole effect, and the 1,2, 3-triazole is often used as a pharmacophore and is introduced into the existing drugs or lead compounds to improve the pharmacological activity (Scheme 1)[4,5]. The compounds are widely applied in the fields of biological medicine, pesticide, material, catalysis and the like. Numerous triazole derivatives are widely used in clinical application as antibacterial, anti-tumor, anti-inflammatory and anti-hypertension drugs[6-9]。
Due to the particularity of the 1,2, 3-triazole ring structure, the synthesis of 1,2, 3-triazole sometimes needs an alkyne source or an azide source with a special structure, and the 1,2, 3-triazole compound usually takes nitrobenzene compounds as raw materials, is reduced into nitro, is subjected to diazotization to prepare an organic azide intermediate, and then reacts with the alkyne compound to prepare the organic azide intermediate[10]. The synthesis method relates to diazotization reaction, and the intermediate is an organic azide which has certain danger. And if the initial raw material is nitrobenzaldehyde compound, the reaction is easy to self-condense in the reduction process, so that the reaction efficiency is reduced[11]And the source of the starting alkyne is not extensive.
Reference documents:
[1]Rostovtsev V,Fokin V,Sharpless K,et al..Angew Chem Int Ed,2002,41(14):2596.
[2]Liu X,Su C H.Synthetic Commun,2017,47(4):279.
[3]Huang Q,Zheng M,Yang S,et al.Eur J Med Chem，2011，46(11):5680.
[4] jiashuhong, Li Cuiping, He xing, et al chemical research and applications, 2016,28(2):158.
[5]Mallemula V R,Sanghai N N,Himabindu V,et al.Res Chem Intermed,2015,41(4):2125.
[6]Ferreira M L G,Pinheiro L C S,Santos-Filho O A,et al.Med Chem Res,2014,23(3):1501.
[7]Santagati N A,Bousquet E,Spadaro A et a1.Farmaco.1999,54,780.
[8]Ram V J,Farhanullah,Tripathi B K et a1.Bioorg.Med.Chem.2003,11,2439.
[9]Alam M S,Kajiki R,Hanatani H et a1.J.Agric.Food Chem.2006,54,1361.
[10]Richard W,Wand Lahti P M.Synthetic Commun,1998,1087.
[11] Jiangyu Bobo, Zhao fen, Hanchun Mei, et al, chemical research and application, 2014,26(12):1831.
Disclosure of Invention
The invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which overcomes the defects of the prior art.
In order to realize the purpose, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, and the structural general formula of the synthesized 1,2, 3-triazole is as follows:
in the formula, R1Is any one of aryl and substituted aryl, R2Is an electron withdrawing group;
wherein "substituted" in the present invention means substituted with one or more of the following substituents: alkyl, alkenyl, alkynyl, alkoxy, halogen, nitro, aryl, heterocyclic, nitrile, isonitrile, hydroxyl, amino, carboxyl, oxo, alkanoyl, alkoxycarbonyl, alkenyloxy, alkylamido and the like.
The synthesis method comprises the following steps: adding a 2, 2-dibromo vinyl benzene compound, sodium azide, a nitrobenzene compound, alkali, a catalyst and sodium ascorbate into a reaction vessel containing an organic solvent; reacting under the protection of nitrogen; after the reaction is finished, carrying out post-treatment, and then carrying out recrystallization or silica gel column chromatography separation and purification to obtain the 1,2, 3-triazole compound; the catalyst is a salt of a monovalent or divalent copper.
Wherein, the 2, 2-dibromo vinyl benzene compound is 2, 2-dibromo vinyl benzene or substituted benzene/pyridine compounds containing 2, 2-dibromo vinyl groups. The nitrobenzene compounds are compounds containing nitrobenzene groups.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the reaction temperature is 25-100 ℃; the reaction time is 2-8 hours. Stirring is carried out during the reaction process.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein R1 in the structural general formula of the synthesized 1,2, 3-triazole is substituted or unsubstituted phenyl, naphthyl or pyridyl.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein R2 in the structural general formula of the synthesized 1,2, 3-triazole is any one of nitryl, aldehyde group, cyano group, carboxyl group and ketone group
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the 2, 2-dibromovinylbenzene compound is any one of 2, 2-dibromovinylbenzene, 4- (2, 2-dibromovinyl) ethylbenzene, (2, 2-dibromovinyl) -3-methoxybenzene, 4- (2, 2-dibromovinyl) butylbenzene, 3- (2, 2-dibromovinyl) pyridine and 4- (2, 2-dibromovinyl) chlorobenzene.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the nitrobenzene compound is any one of 4-nitroacetophenone, 3-nitrobenzoic acid, 4-nitrobenzaldehyde, 3-nitrobenzaldehyde, 2-nitrobenzaldehyde and 4-cyanonitrobenzene.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the base is any one of 1, 5-diazabicyclo [5.4.0] undec-5-ene, potassium sulfide, sodium sulfide and potassium carbonate.
Preferably, the base is 1, 5-diazabicyclo [5.4.0] undec-5-ene, which results in high product yields.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein, the molar ratio of the nitrobenzene compounds to the sodium azide, the 2, 2-dibromo vinyl benzene compounds, the alkali, the catalyst and the sodium ascorbate is 1: 1.2-2: 1-1.5: 1-2: 0.2-1: 0.2 to 1.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the organic solvent is one or a mixture of hexamethylphosphoric triamide, N-dimethylformamide, acetonitrile, N-pyrrolidone or dimethyl sulfoxide; the volume ratio of the substance amount of the nitrobenzene compounds to the organic solvent is 1: 25 to 50.
Further, the invention provides a method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method, which can also have the following characteristics: wherein the post-treatment comprises the following specific steps: after the reaction is finished, insoluble substances are removed by suction filtration, 100-150mL ethyl acetate is added, the mixture is washed for 2 times by saturated saline, the organic phase is dried by a drying agent, then the drying agent is removed by suction filtration, and the filtrate is dried by rotation.
The invention has the beneficial effects that: the invention provides a method for preparing 1,2, 3-triazole by a one-pot method of dibromovinylbenzene, which adopts the one-pot method to prepare, avoids diazotization reaction, does not directly use organic azide, does not pass through the process of reducing nitro into amine, and has high safety, simple operation and mild conditions; and alkyne is not used as a raw material, the raw material source is wide, the cost is low, the industrial production is easy, and the preparation is convenient and safe to purchase. In addition, the method adopts the 2, 2-dibromo vinyl benzene compound and the nitrobenzene compound as synthesis raw materials, so that the synthesized 1,2, 3-triazole can have various substituent groups with different functions, side reactions such as condensation and the like which are not beneficial to product generation can not occur in the synthesis process, and the multifunctional multi-substituent 1,2, 3-triazole can meet various requirements of multi-field drug production and is wide in application.
Detailed Description
Example 1
Preparation of (1- (4-ethyl phenyl) -4-phenyl) -1,2, 3-triazole
To a round-bottomed flask containing 30mL of hexamethylphosphoric triamide were added 165mg (1mmol) of 4-nitroacetophenone, 78mg (1.2mmol) of sodium azide, 262mg (1mmol) of 2, 2-dibromovinylbenzene, 152mg (1mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 99mg (0.5mmol) of sodium ascorbate, and 125mg (0.5mmol) of copper sulfate pentahydrate, and the mixture was stirred at 60 ℃ under nitrogen for 2 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 150mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product is purified by recrystallization to obtain 224mg of off-white solid with the yield of 85.1 percent.
The hydrogen spectral data are characterized as follows:
1H NMR(500MHz,DMSO-d6):δ2.44(m,3H),7.34(t,J＝7.3Hz,1H),7.45(m,2H),7.90(d,J＝7.9Hz,2H),8.06(d,J＝8.7Hz,2H),8.14(d,J＝8.7Hz,2H),9.38(s,1H).MS(ESI):m/z 264(M+H)+.
example 2
Preparation of (1- (4-aldehyde phenyl) -4- (4-ethyl phenyl)) -1,2, 3-triazole
Into a round-bottomed flask containing 30mL of hexamethylphosphoric triamide were charged 151mg (1mmol) of 4-nitrobenzaldehyde, 98mg (1.5mmol) of sodium azide, 290mg (1mmol) of 4- (2, 2-dibromovinyl) ethylbenzene, 228mg (1.5mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 99mg (0.5mmol) of sodium ascorbate, and 96mg (0.5mmol) of cuprous iodide, and the mixture was heated to 40 ℃ and stirred under nitrogen for 6 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain a off-white solid of 234mg with a yield of 84.6%.
The hydrogen spectral data are characterized as follows:
1H NMR(400MHz,CDCl3):δ10.10(s,1H),8.27(s,1H),8.10(d,J＝8.6Hz,2H),8.04(d,J＝8.6Hz,2H),7.85(d,J＝8.1Hz,2H),7.33(d,J＝8.1Hz,2H),2.72(q,J＝7.6Hz,2H),1.30(t,J＝7.6Hz,3H).MS(ESI):m/z 278(M+H)+.
example 3
Preparation of (1- (3-carboxyphenyl) -4- (3-methoxyphenyl)) -1,2, 3-triazole
167mg (1mmol) of 3-nitrobenzoic acid, 130mg (2mmol) of sodium azide, (350 mg (1.2mmol) of 2, 2-dibromoethenyl) -3-methoxybenzene, 110mg (1mmol) of sodium sulfide, 198mg (1mmol) of sodium ascorbate and 125mg (0.5mmol) of copper sulfate pentahydrate are added to a round-bottomed flask containing 30mL of a mixed solution of hexamethylphosphoric triamide and dimethyl sulfoxide (volume ratio of 1:1), and the mixture is heated to 40 ℃ and stirred under nitrogen for reaction for 8 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 100mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain a off-white solid (245 mg) with a yield of 83.2%.
The hydrogen spectral data are characterized as follows:
1H NMR(500MHz,DMSO-d6):δ3.87(s,3H),6.94(dd,J＝8.2,1.8Hz,1H),7.38(t,J＝7.9Hz,1H),7.52(s,1H),7.54(s,1H),,7.92(s,2H),8.07(d,J＝6.1Hz,1H),8.44(s,1H),9.18(s,1H).MS(ESI):m/z 294(M-H)+.
example 4
Preparation of (1- (4-cyanophenyl) -4- (4-butylphenyl)) -1,2, 3-triazole
A round-bottomed flask containing 25mL of dimethyl sulfoxide was charged with 148mg (1mmol) of 4-cyanonitrobenzene, 130mg (2mmol) of sodium azide, 318mg (1.5mmol) of 4- (2, 2-dibromoethenyl) butylbenzene, 110mg (1mmol) of sodium sulfide, 79mg (0.4mmol) of sodium ascorbate, and 76mg (0.4mmol) of cuprous iodide, and the mixture was heated to 100 ℃ and stirred under nitrogen for 6 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 100mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain 237mg of pale yellow solid with a yield of 78.3%.
The hydrogen spectral data are characterized as follows:
1H NMR(300MHz,DMSO-d6):δ0.92(t,J＝7.3Hz,3H),1.33(m,J＝7.3Hz,2H),1.60(q,J＝7.3Hz,2H),2.64(t,J＝7.3Hz,2H),7.34(d,J＝8.0Hz,2H),7.87(d,J＝8.0Hz,2H),8.15(d,J＝8.6Hz,2H),8.22(d,J＝8.6Hz,2H),9.39(s,1H).MS(ESI):m/z 303(M+H)+.
example 5
Preparation of (1- (4-aldehyde phenyl) -4-phenyl) -1,2, 3-triazole
Into a round-bottomed flask containing 30mL of N-pyrrolidone were added 151mg (1mmol) of 4-nitrobenzaldehyde, 130mg (2mmol) of sodium azide, 393mg (1.5mmol) of 2, 2-dibromovinylbenzene, 304mg (2mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 99mg (0.5mmol) of sodium ascorbate, and 125mg (0.5mmol) of copper sulfate pentahydrate, and the mixture was heated to 80 ℃ and stirred under nitrogen for reaction for 8 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain 191mg of off-white solid with a yield of 76.9%.
The hydrogen spectral data are characterized as follows:
1H NMR(400MHz,CDCl3):δ10.12(s,1H),8.32(s,1H),8.12(d,J＝8.5Hz,2H),8.06(d,J＝8.5Hz,2H),7.95(d,J＝7.5Hz,2H),7.51(t,J＝7.5Hz,2H),7.43(t,1H).MS(ESI):m/z 250(M+H)+.
example 6
Preparation of (1- (3-aldehyde phenyl) -4-phenyl) -1,2, 3-triazole
Into a round-bottomed flask containing 25mL of hexamethylphosphoric triamide were added 151mg (1mmol) of 3-nitrobenzaldehyde, 130mg (2mmol) of sodium azide, 262mg (1.5mmol) of 2, 2-dibromovinylbenzene, 304mg (1mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 16mg (0.2mmol) of sodium ascorbate, and 16mg (0.2mmol) of cuprous iodide, and the mixture was heated to 25 ℃ and stirred under nitrogen for 2 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain a off-white solid of 219mg with a yield of 88.3%.
The hydrogen spectral data are characterized as follows:
1H NMR(500MHz,CDCl3):δ10.14(s,1H),8.32(d,J＝7.61Hz,2H),8.20(d,J＝7.2Hz,1H),7.98(d,J＝7.6Hz,1H),7.94(d,J＝7.2Hz,2H),7.78(t,J＝8.0Hz,1H),7.51(t,J＝5.6Hz,2H),7.42(t,J＝4.0Hz,1H)；MS(ESI):m/z 250(M+H)+.
example 7
Preparation of (1- (2-aldehyde phenyl) -4-phenyl) -1,2, 3-triazole
A round-bottomed flask containing 30mL of hexamethylphosphoric triamide was charged with 151mg (1mmol) of 2-nitrobenzaldehyde, 78mg (1.2mmol) of sodium azide, 262mg (1mmol) of 2, 2-dibromovinylbenzene, 138(1mmol) of potassium carbonate, 198mg (1mmol) of sodium ascorbate, and 191mg (1mmol) of cuprous iodide, heated to 100 ℃ and stirred under nitrogen for 6 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain a white-like solid (162 mg) with a yield of 65.3%.
The hydrogen spectral data are characterized as follows:
1H NMR(400MHz,CDCl3):δ9.99(s,1H),8.22(s,1H),8.12(d,J＝7.5Hz,1H),7.93(d,J＝7.3Hz,2H),7.83-7.74(m,1H),7.72-7.62(m,1H),7.58(d,J＝7.7Hz,1H),7.53-7.44(m,2H),7.41(d,J＝7.0Hz,1H).MS(ESI):m/z 250(M+H)+.
in this example, the alkali potassium carbonate may be replaced with potassium sulfide.
Example 8
Preparation of (1- (4-aldehyde phenyl) -4- (3-pyridyl)) -1,2, 3-triazole
Into a round-bottomed flask containing 30mL of hexamethylphosphoric triamide were added 151mg (1mmol) of 4-nitrobenzaldehyde, 130mg (2mmol) of sodium azide, 262mg (1mmol) of 3- (2, 2-dibromovinyl) pyridine, 304mg (1mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 99mg (0.5mmol) of sodium ascorbate, and 96mg (0.5mmol) of cuprous iodide, and the mixture was heated to 60 ℃ and stirred under nitrogen for 4 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain 178mg of a yellow solid with a yield of 71.2%.
The hydrogen spectral data are characterized as follows:
1H NMR(400MHz,CDCl3):δ10.12(s,1H),9.13(s,1H),8.66(d,J＝8.0Hz,1H),8.42(s,1H),8.33(d,J＝8.0Hz,1H),8.13(d,J＝8.5Hz,2H),8.06(d,2H),7.46(m,1H).MS(ESI):m/z 251(M+H)+.
example 9
Preparation of (1- (4-aldehyde phenyl) -4- (4-chlorphenyl)) -1,2, 3-triazole
Into a round-bottomed flask containing 50mL of hexamethylphosphoric triamide were added 151mg (1mmol) of 4-nitrobenzaldehyde, 98mg (1.5mmol) of sodium azide, 296mg (1mmol) of 2, 2-dibromovinylbenzene, 228mg (1.5mmol) of 1, 5-diazabicyclo [5.4.0] undec-5-ene, 99mg (0.5mmol) of sodium ascorbate, and 96mg (0.5mmol) of cuprous iodide, and the mixture was heated to 40 ℃ and stirred under nitrogen for 6 hours. After completion of the reaction, insoluble matter was removed by suction filtration, 120mL of ethyl acetate was added, the mixture was washed with saturated brine 2 times, and the organic phase was dried over a drying agent. And (4) filtering to remove the drying agent, and spin-drying the filtrate. The obtained product was purified by silica gel column chromatography to obtain off-white solid 228mg with a yield of 80.6%.
The hydrogen spectral data are characterized as follows:
1H NMR(400MHz,CDCl3):δ10.12(s,1H),8.31(s,1H),8.12(d,J＝8.0Hz,2H),8.04(d,J＝8.0Hz,2H),7.88(d,J＝8.1Hz,2H),7.48(d,J＝8.1Hz,2H).13C NMR(100MHz,CDCl3):δ190.62,147.94,136.11,131.44,129.93,129.54,129.28,127.19,125.39,120.47,117.33.MS(ESI):m/z 284(M+H)+.
in this embodiment, the organic solvent hexamethylphosphoric triamide can be replaced by N, N-dimethylformamide or acetonitrile; the 2, 2-dibromo vinyl benzene compound 2, 2-dibromo vinyl benzene can also be replaced by 4- (2, 2-dibromo vinyl) chlorobenzene.
Claims (5)
1. A method for preparing 1,2, 3-triazole by a dibromovinylbenzene one-pot method is characterized by comprising the following steps:
the structural general formula of the synthesized 1,2, 3-triazole is as follows:
in the formula, R1Is substituted or unsubstituted phenyl, naphthyl, pyridyl, R2Is any one of nitro, aldehyde group, cyano, carboxyl and ketone group;
the synthesis method comprises the following steps:
adding a 2, 2-dibromo vinyl benzene compound, sodium azide, a nitrobenzene compound, alkali, a catalyst and sodium ascorbate into a reaction vessel containing an organic solvent;
reacting under the protection of nitrogen, wherein the reaction temperature is 25-100 ℃, and the reaction time is 2-8 hours;
after the reaction is finished, carrying out post-treatment, and then carrying out recrystallization or silica gel column chromatography separation and purification to obtain the 1,2, 3-triazole compound;
the catalyst is a cuprous salt or a cupric salt;
the 2, 2-dibromovinylbenzene compound is any one of 2, 2-dibromovinylbenzene, 4- (2, 2-dibromovinyl) ethylbenzene, (2, 2-dibromovinyl) -3-methoxybenzene, 4- (2, 2-dibromovinyl) butylbenzene, 3- (2, 2-dibromovinyl) pyridine and 4- (2, 2-dibromovinyl) chlorobenzene;
the alkali is any one of 1, 5-diazabicyclo [5.4.0] undec-5-ene, potassium sulfide, sodium sulfide and potassium carbonate.
2. The method for preparing 1,2, 3-triazole by the dibromovinylbenzene one-pot method according to claim 1, which is characterized in that:
wherein the nitrobenzene compounds are any one of 4-nitroacetophenone, 3-nitrobenzoic acid, 4-nitrobenzaldehyde, 3-nitrobenzaldehyde, 2-nitrobenzaldehyde and 4-cyanonitrobenzene.
3. The method for preparing 1,2, 3-triazole by the dibromovinylbenzene one-pot method according to claim 1, which is characterized in that:
wherein the molar ratio of the nitrobenzene compound to the sodium azide to the 2, 2-dibromo vinyl benzene compound to the alkali to the catalyst to the sodium ascorbate is 1: 1.2-2: 1-1.5: 1-2: 0.2-1: 0.2 to 1.
4. The method for preparing 1,2, 3-triazole by the dibromovinylbenzene one-pot method according to claim 1, which is characterized in that:
wherein the organic solvent is one or a mixture of several of hexamethylphosphoric triamide, N-dimethylformamide, acetonitrile, N-pyrrolidone or dimethyl sulfoxide;
the volume ratio of the substance amount of the nitrobenzene compounds to the organic solvent is 1: 25 to 50.
5. The method for preparing 1,2, 3-triazole by the dibromovinylbenzene one-pot method according to claim 1, which is characterized in that:
wherein the post-treatment comprises the following specific steps: after the reaction is finished, insoluble substances are removed by suction filtration, 100-150mL ethyl acetate is added, the mixture is washed for 2 times by saturated saline, the organic phase is dried by a drying agent, then the drying agent is removed by suction filtration, and the filtrate is dried by rotation.
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| CN102127024A (en) * | 2011-01-20 | 2011-07-20 | 同济大学 | Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin |
| CN103058942A (en) * | 2012-12-20 | 2013-04-24 | 江苏城市职业学院 | One-pot synthetic method for 1,2,3-triazole compounds |
| CN106588788A (en) * | 2016-11-11 | 2017-04-26 | 河南师范大学 | Method for synthesizing 1,2,3-triazole compound through one-pot two-step method |
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| CN102127024A (en) * | 2011-01-20 | 2011-07-20 | 同济大学 | Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin |
| CN103058942A (en) * | 2012-12-20 | 2013-04-24 | 江苏城市职业学院 | One-pot synthetic method for 1,2,3-triazole compounds |
| CN106588788A (en) * | 2016-11-11 | 2017-04-26 | 河南师范大学 | Method for synthesizing 1,2,3-triazole compound through one-pot two-step method |
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