- Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.
Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.
Journal of the American Chemical Society (2013-03-13)
Stepan Chuprakov, Sen Wai Kwok, Valery V Fokin
PMID23477345
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.