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Method for preparation of 1, 4-substituted 1, 2, 3-triazole from an organic azide compound and (Z)-beta-alkenylbromide and use thereof

A technology of azide compound and alkenyl bromide, which is applied in the field of preparation of 1,2,3-triazole, can solve the problems of high cost and long reaction time, and achieve fast reaction speed, low reaction cost and high product purity Effect

Inactive Publication Date: 2017-06-20
LESHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above method has the disadvantages of reaction, long reaction time, high cost, etc., and the raw material terminal alkyne needs to be synthesized in multiple steps, and therefore it is necessary to find a method that is easy to obtain raw materials, easy to operate, and environmentally friendly to synthesize 1,2,3-triazine Azole compounds are still the goal pursued by many researchers worldwide

Method used

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  • Method for preparation of 1, 4-substituted 1, 2, 3-triazole from an organic azide compound and (Z)-beta-alkenylbromide and use thereof
  • Method for preparation of 1, 4-substituted 1, 2, 3-triazole from an organic azide compound and (Z)-beta-alkenylbromide and use thereof
  • Method for preparation of 1, 4-substituted 1, 2, 3-triazole from an organic azide compound and (Z)-beta-alkenylbromide and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Example 1: Add 1.2mmol of benzyl azide, 1.0mmol of (E)-β-phenylalkenyl bromide, 3.0mmol of DBU, and 0.20mmol of cuprous iodide into 2mL of DMF, stir and react at 100°C for 20min, and the reaction ends After the product is subjected to column chromatography V 石油醚 :V 乙酸乙酯 = 3:1 treatment gives 1-benzyl-4-phenyl 1,2,3-triazole. The product is a white solid, yield: 90%.

Embodiment 2

[0037] Example 2: Add 1.2mmol of 3-trifluoromethylbenzyl azide, 1.0mmol of (E)-β-phenylalkenyl bromide, 3.0mmol of DBU, and 0.20mmol of cuprous iodide into 2mL of DMF, at 100°C Stirring reaction 20min, after reaction finishes, product is through column chromatography V 石油醚 :V 乙酸乙酯 = 3:1 treatment gives 1-(3-trifluoromethylbenzyl)-4-phenyl 1,2,3-triazole. The product is a white solid, yield: 94%.

Embodiment 3

[0038] Example 3: Add 1.2mmol of 4-methoxybenzyl azide, 1.0mmol of (E)-β-phenylalkenyl bromide, 3.0mmol of DBU, and 0.20mmol of cuprous iodide into 2mL of DMF, and stir at 100°C Reaction 20min, after reaction finishes product through column chromatography V 石油醚 :V 乙酸乙酯 = 3:1 treatment gives 1-(4-methoxybenzyl)-4-phenyl 1,2,3-triazole. The product is a white solid, yield: 93%.

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Abstract

The invention relates to a method for preparation of 1, 4-substituted 1, 2, 3-triazole from an organic azide compound and (Z)-beta-alkenylbromide and a use thereof and belongs to the technical field of preparation of 1, 4-substituted 1, 2, 3-triazole. The method comprises that an organic azide compound (1) and (Z)-beta-alkenylbromide (2) as raw materials undergo a reaction at a certain temperature in the presence of an organic solvent-copper catalyst-alkali system to produce a product and the product is separated and purified. The method has the advantages of raw material easy availability, low cost, less pollution, high yield, simple post-treatment process, high product purity and mild reaction conditions, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of 1,2,3-triazoles, in particular to an organic azide compound and (Z)-β-alkenyl bromide to prepare 1,4-substituted 1,2,3-triazoles methods and applications. Background technique [0002] 1,2,3-Triazole is a very important class of nitrogen-containing compounds, which are widely used in industry as pigments, fiber brighteners, metal alloy preservatives, organic matter and polymer stabilizers. It is used in herbicides and fungicides in medicine, and it is used in a variety of drugs with different functions in medicine. Since such compounds do not exist in nature, they are generally prepared by chemical methods. [0003] In recent years, many research groups have reported the synthesis method of 1,2,3-triazole. The most commonly used method for preparing 1,2,3-triazole is: terminal alkyne and organic azide two components in Synthesis of 1,2,3-triazole under the condition of catalyst (usually ...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D405/04C07H19/056C07H1/00
CPCC07D249/06C07D405/04C07H1/00C07H19/056
Inventor 曾鸿耀仲昱洁高志磊李丽王应红夏烈文何云清田冲胡育
Owner LESHAN NORMAL UNIV
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