Acetylacetone copper (II) catalytic synthesis method for 1,2,3 triazole chemical compounds

A technology of copper acetylacetonate and azide compounds, which is applied in the field of synthesis of 1,2,3-triazole compounds, can solve the problems of difficult preparation of metal catalysts, tedious multi-step synthesis, and difficulty in recycling, and achieve cheap catalysts , environmental friendliness and short response time

Inactive Publication Date: 2015-09-30
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above reactions of using Cu as a catalyst to catalyze the synthesis of 1,2,3-triazole compounds, metal catalysts are not easy to obtain, are easily deactivated and difficult to recycle, and most of the solvents used are organic reagents. Multi-step synthesis, other special reagents are added

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 10g (0.041mol) Cu(NO 3 ) 2 ·3H 2 O was dissolved in 100mL of water, and 15mL of concentrated ammonia water was added to obtain copper ammonia complex ion [Cu(NH 3 ) 4 ] 2+ Add 11 mL of acetylacetone under stirring to obtain a blue precipitate, filter and wash with water, and dry in vacuo to obtain 10.05 g of a blue powdery crude product. The crude product is refluxed and dissolved with a mixed solution of 75 mL of chloroform and 225 mL of methanol, cooled, crystallized and dried to obtain 7.48 g blue crystal copper (II) acetylacetonate for later use.

Embodiment 2

[0022] Using the copper (II) acetylacetonate obtained in Example 1 as the catalyst, add 0.0065 g (0.025 mmol) of the catalyst copper (II) acetylacetonate, 0.066 g (0.5 mmol) of phenoxypropyne, phenyl azide 0.060g (0.5mmol) and 2mL of water were stirred and reacted in an oil bath at 50°C, and the reaction process was monitored by TLC. TLC monitors that the reaction is complete in 0.5h, adding ethyl acetate for extraction, filtering the aqueous phase and the organic phase at the same time, washing the filter cake with ethyl acetate, the filter cake is blue, and there is no significant change before and after the catalyst reaction, the filtrate is separated, and organic Phase sampling was done to analyze the product by HPLC. The influence of different solvents on the reaction is shown in Table 1.

[0023] Table 1 The influence of different solvents on the reaction

[0024] .

Embodiment 3

[0026]The copper (II) acetylacetonate regenerated in Example 2 was used as the catalyst, and 0.026 g (0.1 mmol) of the recovered catalyst copper (II) acetylacetonate, 0.066 g (0.5 mmol) of phenoxypropyne, phenyl Azide 0.071g (0.6mmol) and water 2mL were stirred and reacted in an oil bath at 50°C, and the reaction process was monitored by TLC. TLC monitors that the reaction is complete after 0.5h, add ethyl acetate for extraction, filter the water phase and the organic phase simultaneously, wash the filter cake (catalyst) with ethyl acetate, separate the filtrate, take a sample of the organic phase for HPLC analysis of the product, and repeat the recovery The effect of the number of times on the reaction yield is shown in Table 2.

[0027] Table 2 The effect of the number of repetitions on the reaction yield

[0028] .

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Abstract

The invention discloses an acetylacetone copper (II) catalytic synthesis method for 1,2,3 triazole chemical compounds, and belongs to the field of the synthetic technology of the 1,2,3 triazole chemical compounds. According to the technical scheme, azide and end group compound serve as raw materials, the acetylacetone copper (II) serves as a catalyzer, water serves as a solvent, stirring and reacting are conducted, complete reaction of the raw materials is monitored by TLC, ethyl acetate is added to extract a reaction product, water phase and organic phase are filtered at the same time, a filter cake is cleaned by using the ethyl acetate to obtain the catalyzer, namely, the acetylacetone copper (II) to be recycled repeatedly, and skimming is conducted on filter liquor to obtain the organic phase of the 1,2,3 triazole chemical compound. The catalyzer is cheap, the preparation method is simple, the catalytic efficiency is high, reutilization can be achieved, the catalyzer is reproducible, the reproductive catalyzer still has high catalytic activity, and the yield of the product is equal to the catalyzer before reproduction is conducted.

Description

technical field [0001] The invention belongs to the technical field of synthesis of 1,2,3-triazole compounds, and in particular relates to a method for catalyzing the synthesis of 1,2,3-triazole compounds by copper (II) acetylacetonate. Background technique [0002] 1,2,3-Triazole is one of the most valuable compounds and has been widely used in various fields of chemistry, such as medicinal chemistry, agricultural chemistry, and material chemistry. The intermediate triazole is one of the basic modules for building molecules, not only an important intermediate in organic synthesis, but also the basic skeleton of physiologically active compounds. Cycloaddition reaction is one of the very important and classic reactions in organic chemistry. Since Huisgen proposed the concept of 1,3-dipolar cycloaddition, 1,3-dipolar cycloaddition has become a general method for the synthesis of five-membered heterocyclic compounds. The research on cycloaddition reactions has a history of ma...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D249/04
CPCC07D249/04C07D249/06
Inventor 姜玉钦李兴丰郭妞何兴董文佩毛龙飞徐桂清李伟
Owner HENAN NORMAL UNIV
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