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

Authors :
Chuprakov S
Kwok SW
Fokin VV
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2013 Mar 27; Vol. 135 (12), pp. 4652-5. Date of Electronic Publication: 2013 Mar 15.
Publication Year :
2013

Abstract

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.

Details

Language :
English
ISSN :
1520-5126
Volume :
135
Issue :
12
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
23477345
Full Text :
https://doi.org/10.1021/ja400350c