title: Efficient synthesis of 1,2,3-triazoles by copper-mediated C-N and N-N bond formation starting from N-tosylhydrazones and amines.
abstract: An effective copper-mediated synthesis of 1,5-dialkyl-4-aryl-1,2,3-triazoles and 1,4-dialkyl-5-aryl-1,2,3-triazoles has been achieved by the use of different N-tosylhydrazones and alkyl amines. The scope of the substrates could be extended from anilines to aliphatic amines when 30 mol % amino acid is added into the reaction mixture. This methodology exhibits many notable features, such as broad substrates scope, high efficiency, and good regioselectivity. Preliminary mechanistic studies indicated that the reaction probably proceeded through a 1-tosyl-2-vinyldiazene intermediate and subsequent aza-Michael addition and N-N bond formation process.
authors.affiliation: ZJU-NHU United R&D Center, Department of Chemistry, Zhejiang University, Hangzhou 310027 (P. R. China).
authors.forename: Zhengkai
authors.initials: Z
authors.lastname: Chen
authors.forename: Qiangqiang
authors.initials: Q
authors.lastname: Yan
authors.forename: Hong
authors.initials: H
authors.lastname: Yi
authors.forename: Zhanxiang
authors.initials: Z
authors.lastname: Liu
authors.forename: Aiwen
authors.initials: A
authors.lastname: Lei
authors.forename: Yuhong
authors.initials: Y
authors.lastname: Zhang
keywords: CN bond formation; NN bond formation; amines; copper; triazoles