Method for synthesizing 1, 4-bis-substituted-1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and sulfonyl azide

Abstract

The invention discloses a method for synthesizing 1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and azide. According to the method, propargyl esters, primary amine and sulfonyl azide serve as raw materials, the enaminone with an NH structure is generated in situ, the raw materials are stirred at room temperature for two hours under catalysis of secondary amine and sodium tert-butoxide, 1, 4-bis-substituted-1, 2, 3-triazole compounds can be obtained with high yield, and products are subjected to chromatographic purification by a silica gel column. The method has the advantages that reaction conditions are mild, reaction can be smoothly realized at the room temperature, reaction time is short, two steps can be finished totally for four hours, the raw materials are green and low in cost, ferric chloride used in first-step operation is an environment-friendly catalyst, metal is omitted in second-step reaction, the method is greener than most methods for synthesizing similar compounds, and the method is simple in overall operation and suitable for large-scale production.

Description

technical field [0001] The invention relates to a method for synthesizing 1,4-disubstituted-1,2,3-triazole by base-catalyzed enaminone and sulfonyl azide cycloaddition reaction. Background technique [0002] 1,2,3-Triazoles are common basic structures of heterocyclic compounds, which have important application value in many fields such as biomedicine, materials, and chemical intermediates. Since Sharpless et al. synthesized 1,2,3-triazoles by direct cycloaddition reaction of azides and alkynes via copper catalysis and proposed the concept of "click chemistry" based on the reaction, the synthesis of such compounds and Applied research has made unprecedented progress. In addition to the copper-catalyzed click cycloaddition reaction, other transition metals such as rhodium, ruthenium, iridium, etc. can also be used to catalyze this type of cycloaddition reaction to synthesize 1,2,3-triazole. - triazole compounds. With the current increasing emphasis on sustainable developmen...

AI Technical Summary

Problems solved by technology

Interestingly, the synthesis of 1,4-disubstituted 1,2,3-triazoles via N–N bond cleavage reactions in enaminones and sulfonyl azides has not been reported yet.

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