(z)-β-alkenyl bromide multi-component preparation method and application of 1,4-substituted-1,2,3-triazole

A technology of alkenyl bromide and triazole, applied in the field of preparation of 1,2,3-triazole, to achieve the effect of reducing intermediate treatment process, mild reaction conditions and low price

Inactive Publication Date: 2019-11-12
LESHAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • (z)-β-alkenyl bromide multi-component preparation method and application of 1,4-substituted-1,2,3-triazole
  • (z)-β-alkenyl bromide multi-component preparation method and application of 1,4-substituted-1,2,3-triazole
  • (z)-β-alkenyl bromide multi-component preparation method and application of 1,4-substituted-1,2,3-triazole

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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 Alcohol 400 3.0mL, stirred and reacted at 100°C for 30min, 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 3.0 mL of polyethylene glycol 400 During the reaction at 100°C for 2.0 hours, the product was subjected to column chromatography after the reaction was completed. 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 3.0 mL of polyethylene glycol 400 In, 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 present invention specifically relates to a method and application of (Z)-β-alkenyl bromide multi-component preparation of 1,4-substituted-1,2,3-triazole, belonging to 1,4-substituted-1,2, The technical field of preparation of 3-triazole. The method is as follows: using halide, azide reagent and (Z)-β-alkenyl bromide as raw materials, adding copper catalyst and alkali, stirring and reacting in a solvent at a certain temperature, and separating and purifying the product after the reaction is completed, That is, the 1,4-substituted-1,2,3-triazole is obtained. The raw materials used in the synthesis method of the present invention are easy to obtain, low in cost, mild in reaction conditions, easy to operate, high in yield, environmentally friendly in the reaction process, and 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 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 & AuthorityPatents(China)
IPC IPC(8): C07D249/06C07D249/04C07D405/04C07H1/00C07H19/056
CPCC07D249/04C07D249/06C07D405/04C07H1/00C07H19/056
Inventor曾鸿耀
OwnerLESHAN NORMAL UNIV