Stepan Chuprakov1, Sen Wai Kwok, Valery V Fokin. 1. Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
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.
Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of n class="Chemical">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.
Authors: Hillary J Dequina; Josephine Eshon; William T Raskopf; Israel Fernández; Jennifer M Schomaker Journal: Org Lett Date: 2020-04-22 Impact factor: 6.005