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Transannulation of 1‑Sulfonyl-1,2,3-triazoles with Heterocumulenes

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posted on 19.02.2016, 15:38 by Stepan Chuprakov, Sen Wai Kwok, Valery V. Fokin
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.