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Method for preparing 1,2,3-triazole through dibromo-vinyl benzene one-pot process

A technology of dibromovinylbenzene and dibromoethylene, applied in the direction of organic chemistry and the like, can solve the problems such as insufficient source of raw material alkynes, low reaction efficiency, etc., and achieve the effects of low cost, high safety, and easy industrial production.

Active Publication Date: 2019-05-21
JIANGSU OPEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This kind of synthetic method involves diazotization reaction, and the intermediate is an organic azide compound, which has certain risks
And if the starting material is a nitrobenzaldehyde compound, it is easy to self-condense in the reduction process, resulting in a reduction in reaction efficiency [11] , and the source of the raw alkyne is not extensive

Method used

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  • Method for preparing 1,2,3-triazole through dibromo-vinyl benzene one-pot process
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  • Method for preparing 1,2,3-triazole through dibromo-vinyl benzene one-pot process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of (1-(4-Ethanonylphenyl)-4-phenyl)-1,2,3-triazole

[0038]

[0039]Add 165 mg (1 mmol) of 4-nitroacetophenone, 78 mg (1.2 mmol) of sodium azide, and 262 mg (1 mmol) of 2,2-dibromovinylbenzene into a round-bottomed flask containing 30 mL of hexamethylphosphoric triamide. ), 1,5-diazabicyclo[5.4.0]undec-5-ene 152mg (1mmol), sodium ascorbate 99mg (0.5mmol), copper sulfate pentahydrate 125mg (0.5mmol), nitrogen protection at 60°C The reaction was stirred for 2 hours. After the reaction was completed, insoluble matter was removed by suction filtration, 150 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by recrystallization to obtain 224 mg of off-white solid, with a yield of 85.1%.

[0040] The hydrogen spectrum data are characterized as follows:

[0041] 1 H NMR (500MHz, ...

Embodiment 2

[0043] Preparation of (1-(4-formylphenyl)-4-(4-ethylphenyl))-1,2,3-triazole

[0044]

[0045] Add 151 mg (1 mmol) of 4-nitrobenzaldehyde, 98 mg (1.5 mmol) of sodium azide, and 4-(2,2-dibromoethenyl) ethyl alcohol into a round-bottomed flask containing 30 mL of hexamethylphosphoric triamide. Benzene 290mg (1mmol), 1,5-diazabicyclo[5.4.0]undec-5-ene 228mg (1.5mmol), sodium ascorbate 99mg (0.5mmol), cuprous iodide 96mg (0.5mmol), Heated to 40°C, stirred and reacted for 6 hours under nitrogen protection. After the reaction was completed, insoluble matter was removed by suction filtration, 120 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by silica gel column chromatography to obtain 234 mg of off-white solid with a yield of 84.6%.

[0046] The hydrogen spectrum data are characterized as follo...

Embodiment 3

[0049] Preparation of (1-(3-carboxyphenyl)-4-(3-methoxyphenyl))-1,2,3-triazole

[0050]

[0051] Add 167mg (1mmol) of 3-nitrobenzoic acid and 130mg (2mmol) of sodium azide to a round-bottomed flask containing 30mL of a mixed solution of hexamethylphosphoric triamide and dimethyl sulfoxide (volume ratio: 1:1). ), (2,2-dibromovinyl)-3-methoxybenzene 350mg (1.2mmol), sodium sulfide 110mg (1mmol), sodium ascorbate 198mg (1mmol), copper sulfate pentahydrate 125mg (0.5mmol), heating to 40° C., stirred and reacted for 8 hours under nitrogen protection. After the reaction was completed, insoluble matter was removed by suction filtration, 100 mL of ethyl acetate was added, washed twice with saturated brine, and the organic phase was dried with a desiccant. The desiccant was removed by suction filtration, and the filtrate was spin-dried. The obtained product was purified by silica gel column chromatography to obtain 245 mg of off-white solid with a yield of 83.2%.

[0052] The hyd...

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Abstract

The invention discloses a method for preparing 1,2,3-triazole through a dibromo-vinyl benzene one-pot process. The synthesis method comprises the following steps that a 2,2-dibromo-vinyl benzene compound, sodium azide, a nitrobenzene compound, alkali, a catalyst and sodium ascorbate are added to a reaction container with an organic solvent; under nitrogen protection, a reaction is conducted; afterthe reaction is ended, aftertreatment is conducted, and then through recrystallization or silica gel column chromatography separation and purification, the 1,2,3-triazole compound is obtained; a catalyst is cuprous salt or cupric salt. The method has the advantages of being high in safety, easy to operate, mild in condition, low in cost, capable of easily achieving industrial production and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of 1,2,3-triazole, in particular to a method for preparing 1,2,3-triazole by a one-pot method of dibromovinylbenzene. Background technique [0002] 1,2,3-Triazole and its derivatives, as an important part of nitrogen-containing heterocyclic compounds, have not been found in nature, and the main source of such compounds is entirely dependent on artificial synthesis. In 2001, Sharpless et al. found that the transition metal copper can well catalyze the Huisgen1,3-dipolar cycloaddition reaction of organic azides and terminal alkynes, referred to as CuACC reaction. [1] . This type of reaction has wide substrate applicability, fast reaction speed, high yield and good regioselectivity [2] , which is a milestone in the synthesis of 1,2,3-triazole. [0003] 1,2,3-Triazole compounds are a very important class of compounds with aromatic ring stability and good biocompat...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D401/04
Inventor 刘霞苏长会胡大华沈宏潘涛
Owner JIANGSU OPEN UNIV
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