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Efficient Synthesis of 1,2,3-Triazoles by Copper-Mediated CN and NN Bond Formation Starting From N-Tosylhydrazones and Amines

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 i...

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Published in:Chemistry : a European journal 2014-10, Vol.20 (42), p.13692-13697
Main Authors: Chen, Zhengkai, Yan, Qiangqiang, Yi, Hong, Liu, Zhanxiang, Lei, Aiwen, Zhang, Yuhong
Format: Article
Language:English
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Summary: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. A 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 is extended from anilines to aliphatic amines when 30 mol % amino acid is added into the reaction mixture (see scheme). This methodology exhibits many notable features, such as broad substrate scope, high efficiency, and good regioselectivity.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403515