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 Fayol; Christopher Housseman; Xiaowen Sun; Pierre Janvier; Hugues Bienaymé; Jieping Zhu

doi:10.1055/s-2004-831225

PSP

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 Fayol^a, Christopher Housseman^a, Xiaowen Sun^a, Pierre Janvier^a, Hugues Bienaymé^b, 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

Abstract

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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.

Key words

domino process - multicomponent reaction - heterocycles - isonitrile - oxazole - pyrrolopyridinone - tetrahydrofuropyridine

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