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

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.

SUBMITTER: Chuprakov S

PROVIDER: S-EPMC3645925 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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

Chuprakov Stepan S Kwok Sen Wai SW Fokin Valery V VV

Journal of the American Chemical Society 20130315 12

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. ...[more]

PMID: 23477345

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