Synthesis 2005(1): 161-165  
DOI: 10.1055/s-2004-831225
PSP
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α-Isocyano-α-alkyl(aryl)acetamides and their Use in the Multicomponent Synthesis of 5-Aminooxazole, Pyrrolo[3,4-b]pyridin-5-one and 4,5,6,7-Tetrahydrofuro[2,3-c]pyridine

Aude Fayola, Christopher Houssemana, Xiaowen Suna, Pierre Janviera, Hugues Bienayméb, Jieping Zhu*a
a Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: zhu@icsn.cnrs-gif.fr;
b Urogene-Chrysalon, 11, Avenue A. Einstein, 69100 Villeurbanne, France
Further Information

Publication History

Received 26 May 2004
Publication Date:
16 September 2004 (online)

Abstract

α-Isocyano-β-phenylpropionamide 1 is synthesized from the corresponding amino acid in excellent yield. The unique reactivity of this bifunctional compound is exploited for the development of novel multicomponent synthesis of 5-aminooxazole 6, pyrrolo[3,4-b]pyridin-5-one 10 and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine 13.