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. 2013 Mar 27;135(12):4652-5.
doi: 10.1021/ja400350c. Epub 2013 Mar 15.

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

Stepan Chuprakov  1 , Sen Wai Kwok, Valery V Fokin
Affiliations

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

Stepan Chuprakov et al. J Am Chem Soc. .

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.

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Figures

Figure 1
Figure 1
Rhodium(II) carboxylates used in this study.
Scheme 1
Scheme 1
Desulfonylation of Mesyl-Protected Transannulation Products.
See this image and copyright information in PMC

References

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    1. For review, see: Chattopadhyay B, Gevorgyan V. Angew. Chem. Int. Ed. 2012;51:862.

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