Method for synthesizing 1,4-substituted 1,2,3-triazole by alkynoic acid multi-components

A multi-component, triazole technology, applied in the direction of chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of limited application range, long reaction time, large limitations, etc., and achieve easy storage Easy to transport, easy to handle, and easy to synthesize effects

Inactive Publication Date: 2019-12-03
LESHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In summary, the existing problems in the prior art are: the current method of using alkynoic acid to participate in the reaction has long reaction time, low yield, limited scope of application, large limitations, low yield, harsh conditions, and difficult operation. cumbersome

Method used

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  • Method for synthesizing 1,4-substituted 1,2,3-triazole by alkynoic acid multi-components
  • Method for synthesizing 1,4-substituted 1,2,3-triazole by alkynoic acid multi-components
  • Method for synthesizing 1,4-substituted 1,2,3-triazole by alkynoic acid multi-components

Examples

Experimental program
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Effect test

Embodiment 1

[0073] Example 1: Add 1.0mmol of phenylpropiolic acid, 1.5mol of sodium azide, 1.2mmol of m-trifluorobenzyl bromide, 0.2mmol of potassium carbonate, and 0.1mmol of cuprous iodide to polyethylene glycol 4003.0mL, 60 ℃ stirring reaction 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%.

[0074]

Embodiment 2

[0075] Example 2: Add 1.0mmol of phenylpropiolic acid, 1.5mol of sodium azide, 1.2mmol of m-trifluorobenzyl bromide, and 0.1mmol of cuprous iodide into polyethylene glycol 4003.0mL, and stir at 60°C for 2.0h , after the reaction, the product is 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%.

[0076]

Embodiment 3

[0077] Example 3: 1.0mmol of phenylpropiolic acid, 1.5mol of sodium azide, 1.2mmol of m-trifluorobenzyl bromide, and 0.1mmol of cuprous iodide were added to polyethylene glycol 4003.0mL, stirred at room temperature for 25h, and the reaction After the end, 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%.

[0078]

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Abstract

The invention belongs to the technical field of preparation of nitrogen-containing compounds, and discloses a method for synthesizing 1,4-substituted 1,2,3-triazole by alkynoic acid multi-components.The method comprises the following steps: adding 1.2 equivalents of a (pseudo) halide, 1.5 equivalents of an azide reagent, 1.0 equivalent of alkynoic acid, 0.1 equivalent of cuprous iodide, 0.2 equivalent of potassium carbonate or potassium hydroxide and a solvent polyethylene glycol 400 into a reaction bottle, and carrying out stirring for a reaction; after the reaction is determined to be finished by thin layer chromatography plate pointing, adding water, adding ethyl acetate for extraction, combining the ethyl acetate, drying the ethyl acetate layer by anhydrous sodium sulfate, and carrying out concentrating under reduced pressure to obtain a crude product; and performing column chromatography to obtain the corresponding 1,4-substituted 1,2,3-triazole. According to the invention, the target product 1,4-substituted 1,2,3-triazole is synthesized in one step; the toxicity of a used catalyst is low, reaction conditions are mild, operation is simple and convenient, the yield is high, cost is low, and the reaction process is green and environmentally friendly; and thus the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of nitrogen-containing compounds, and in particular relates to a method for synthesizing 1,4-substituted 1,2,3-triazoles from alkynoic acid with multiple components. 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 and alloy preservatives and organic and polymer stabilizers. In agriculture, it is used as herbicide and fungicide, and in medicine, it is used in a variety of drugs with different functions. Since this type of compound does not exist in nature, it is prepared by chemical methods. In recent years, many research groups have reported the synthesis methods of 1,2,3-triazoles. The most common methods for preparing 1,2,3-triazoles include: [0003] The first method: Synthesis of 1,2,3-triazole with two components of terminal alkyne and organic azide under the...

Claims

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Application Information

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