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Three-Component Strategy toward 5-Membered Heterocycles from Isocyanide Dibromides

Laurent El Kaim*, Laurence Grimaud* and Pravin Patil

*Laboratoire Chimie et procedes, Ecole Nationale Superieure de Techniques Avancees, 32 Bd Victor, 75739 Paris Cedex 15, France, Email: laurent.elkaimensta-paristech.fr, laurence.grimaudensta-paristech.fr

L. El Kaim, L. Grimaud, P. Patil, Org. Lett., 2011, 13, 1261-1263.

DOI: 10.1021/ol200003u (free Supporting Information)



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Abstract

Cascade reactions starting from isocyanides allow a straightforward synthesis of five-membered ring heterocycles. Addition of sodium azide on isocyanide dibromides followed by electrocyclization and a Suzuki coupling affords tetrazoles scaffolds, whereas addition of tetrazoles on isocyanide dibromides followed by Huisgen rearrangement and a Suzuki coupling gives triazoles scaffolds.

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Key Words

Tetrazoles, Suzuki Coupling, Heterobiaryls


ID: J54-Y2011-0640