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.elkaim
ensta-paristech.fr, laurence.grimaudensta-paristech.fr
L. El Kaim, L. Grimaud, P. Patil, Org. Lett., 2011, 13, 1261-1263.
DOI: 10.1021/ol200003u
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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
