Synthesis 2009(10): 1635-1638  
DOI: 10.1055/s-0028-1088042
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reaction of Isocyanides, Dialkyl Acetylenedicarboxylates, and α-Keto Lactones: Unexpected Participation of an Ester Carbonyl Group in the Isocyanide-Based Three-Component Reaction

Abbas Ali Esmaeili*, Hamid Vesalipoor
Department of Chemistry, University of Birjand, P. O. Box 97175/615, Birjand, Iran
Fax: +98(561)2502009; e-Mail: aa_esmaeili@yahoo.com;
Further Information

Publication History

Received 24 November 2008
Publication Date:
25 March 2009 (online)

Abstract

The reaction of benzofuran-2,3-dione derivatives with dialkyl acetylenedicarboxylates and alkyl isocyanides results in a three-component addition reaction in which the ester carbonyl group is incorporated into a two-atom assembling unit to give highly functionalized γ-spiroiminolactones in good yield. This reaction provides the first example of an ester carbonyl group participating in an isocyanide-based multicomponent reaction.