Double nucleophilic attack on isocyanide carbon: a synthetic strategy for 7-aza-tetrahydroindoles.

Yifei Li, Xianxiu Xu, Chunyu Xia, Lingjuan Zhang, Ling Pan, Qun Liu

Index: Chem. Commun. (Camb.) 48(100) , 12228-30, (2012)

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Abstract

A novel and efficient route for the synthesis of 7-aza-tetrahydroindoles from N-aryl/alkyl-alkenoylacetamides and ethyl isocyanoacetate is described. A mechanism, involving a stepwise [3+2] cycloaddition-intramolecular aza-Michael addition cascade, is proposed that explains the origin of the double nucleophilic attack on the isocyanide carbon atom.