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Method for preparing 1, 4-substituted-1, 2, 3-triazole from (Z)-beta-alkenyl bromide multicomponents and use thereof

A technology for alkenyl bromide and triazole, which is applied in the field of preparation of 1,2,3-triazole and achieves the effects of short route, high yield and fast reaction speed

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

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  • Method for preparing 1, 4-substituted-1, 2, 3-triazole from (Z)-beta-alkenyl bromide multicomponents and use thereof
  • Method for preparing 1, 4-substituted-1, 2, 3-triazole from (Z)-beta-alkenyl bromide multicomponents and use thereof
  • Method for preparing 1, 4-substituted-1, 2, 3-triazole from (Z)-beta-alkenyl bromide multicomponents and use thereof

Examples

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Embodiment 1

[0044] Example 1: Add 1.0mmol of phenylpropane (Z)-β-alkenyl bromide, 1.2mol of sodium azide, 1.5mmol of m-trifluorobenzyl bromide, 3.0mmol of DBU, and 0.2mmol of cuprous iodide to polyethylene glycol In alcohol 4003.0mL, stirred at 100°C for 30 minutes, after the reaction, the product was subjected to 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: 98%.

Embodiment 2

[0045] Example 2: Add 1.0 mmol of phenylpropane (Z)-β-alkenyl bromide, 1.2 mol of sodium azide, 1.5 mmol of m-trifluorobenzyl bromide, and 0.1 mmol of cuprous iodide to 400 3.0 mL of polyethylene glycol , stirred at 100°C for 2.0h, after the reaction, the product was subjected to 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: 89%.

Embodiment 3

[0046] Example 3: Add 1.0 mmol of phenylpropane (Z)-β-alkenyl bromide, 1.2 mol of sodium azide, 1.5 mmol of m-trifluorobenzyl bromide, and 0.1 mmol of cuprous iodide to 400 3.0 mL of polyethylene glycol , stirred at room temperature and reacted for 25h, after the reaction, the product was subjected to 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: 85%.

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Abstract

The invention relates to a method for preparing 1, 4-substituted-1, 2, 3-triazole from (Z)-beta-alkenyl bromide multicomponents and a use thereof and belongs to the technical field of preparation of 1, 4-substituted-1, 2, 3-triazole. The method comprises that a copper catalyst and a base are added into a halide, an azide reagent and (Z)-beta-alkenyl bromide as raw materials, the mixture is stirred in a solvent at a certain temperature and undergoes a reaction, and the reaction products are separated and purified so that 1, 4-substituted-1, 2, 3-triazole is obtained. The method has the advantages of easy availability of raw materials, low cost, mild reaction condition, simple operation, high yield, environmental friendliness in the reaction process and industrial production feasibility.

Description

technical field [0001] The invention belongs to the technical field of preparation of 1,2,3-triazoles, in particular to a method for preparing 1,4-substituted-1,2,3-triazoles with multiple components of (Z)-β-alkenyl bromide method and application. 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 methods of 1,2,3-triazole. The most commonly used methods for preparing 1,2,3-triazole include: [0004] The first method: Synthesis of 1,2,3-triazole with two components of terminal alkyne and organic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D249/04C07D405/04C07H1/00C07H19/056
CPCC07D249/04C07D249/06C07D405/04C07H1/00C07H19/056
Inventor 曾鸿耀
Owner LESHAN NORMAL UNIV
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