Amine-catalyzed synthesis of N^(2)-sulfonyl 1,2,3-triazole in water and the tunable N^(2)-H 1,2,3-triazole synthesis in DMSO via metal-free enamine annulation  

作　　者：Yanhui Guo Yunyun Liu Jie-Ping Wan 

机构地区：[1]College of Chemistry and Chemical Engineering,Jiangxi Normal University,Nanchang 330022,China

出　　处：《Chinese Chemical Letters》2022年第2期855-858,共4页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China (No.21861019);Natural Science Foundation of Jiangxi Province (No.20202ACBL203006)。

摘　　要：The selective synthesis of N^(2)-sulfonyl and N^(2)-H 1,2,3-triazoles via organocatalytic annulation of enaminone/enaminoester with sulfonyl azide has been realized. The unconventional selectivity providing N^(2)-sulfoyl 1,2,3-triazoles takes place in pure water, wherein the hydrogen bond effect between water and the intermediate resulting from enamine-azide corporation accounts for the novel reaction selectivity. On the other hand, the reactions conducted in DMSO specifically afford N^(2)-H 1,2,3-triazoles in the absence of such hydrogen bond effect.

关 键 词：ENAMINONE ANNULATION N^(2)-sulfonyl 1 2 3-triazole Selectivity Green synthesis Sulfonyl azide 

分 类 号：O626.26[理学—有机化学]