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Synfacts 2006(7): 0655-0655  
DOI: 10.1055/s-2006-941848
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Amino Triazoles by Huisgen [3+2] Cycloaddition

Contributor(s): Victor Snieckus, Todd Macklin
M. IJsselstijn, J. C. Cintrat*
Service de Marquage Moléculaire et de Chimie Bioorganique, Gif sur Yvette, France
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

This constitutes the first report of copper(I)-catalyzed regioselective [3+2] dipolar cycloaddition of ynamides with azides to give 1,4-substituted 1,2,3-triazoles in modest to excellent yields. The original Huisgen reaction involving cycloaddition between an ynamine and an azide gives rise to the 1,5-substituted isomers (G. Himbert, W. Schwickerath Liebigs Ann. Chem. 1982, 12, 2105-2118). The reaction utilizes mild ‘click’ conditions, proceeds from simple building blocks, and tolerates a broad range of functional groups.