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A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles

Jie-Ping Wan*, Shuo Cao and Yunyun Liu

*Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, PR China, Email: wanjiepingjxnu.edu.cn

J.-P. Wan, S. Cao, Y. Liu, J. Org. Chem., 2015, 80, 9028-9033.

DOI: 10.1021/acs.joc.5b01121 (free Supporting Information)


 
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Abstract

The three-component reactions of enaminones, tosylhydrazine and primary amines enabled a regioselective construction of 1,5-disubstituted 1,2,3-triazoles via cascade dual C-N bond formation, N-N bond formation and an acyl migration-based C-C bond formation. This metal- and azide-free method proceeds in the presence of only molecular iodine.

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Key Words

1,2,3-triazoles, multicomponent reactions


ID: J42-Y2015