Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

J Am Chem Soc

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Published: March 2013

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3645925PMC
http://dx.doi.org/10.1021/ja400350cDOI Listing

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