Visible Light-Enhanced [3 + 2] Cycloaddition of N,N‑Disubstituted Hydrazines with Organo-Cyanamides: Access to Polysubstituted 1,2,4-Triazol-3-amines

Visible light-enhanced [3 + 2] cycloaddition of N,N-disubstituted hydrazines with N-cyano-N-aryl-p-toluenesulfonamides is an efficient reaction pathway to polysubstituted 1,2,4-triazol-3-amines. The reaction is performed under mild conditions without the addition of any transition metals. This strat...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-01, Vol.89 (2), p.994-1009
Main Authors: Zhuo, Xiaoya, Zheng, Lvyin, Liu, Yujie, Wang, Yihan, Zou, Xiaoying, Zhong, Yumei, Guo, Wei
Format: Article
Language:English
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Summary:Visible light-enhanced [3 + 2] cycloaddition of N,N-disubstituted hydrazines with N-cyano-N-aryl-p-toluenesulfonamides is an efficient reaction pathway to polysubstituted 1,2,4-triazol-3-amines. The reaction is performed under mild conditions without the addition of any transition metals. This strategy involves a C­(sp3)–H bond activation, a cyano cycloaddition, and the formation of two new CN bonds. The protocol shows the advantages of good functional group tolerance and broad substrate scope. The late-stage modification experiments provide practical applications in the field of organic synthesis and medicinal chemistry.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02085