Tetrahedron

Diels-Alder reactions of 1, 5-dihydropyrano [3, 4-b] pyrrol-5 (1H)-ones, pyrrole-2, 3-quinodimethane analogues; a new synthesis of indoles

PM Jackson, CJ Moody

Index: Mark Jackson; Moody, Christopher J. Tetrahedron, 1992 , vol. 48, # 36 p. 7447 - 7466

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Citation Number: 19

Abstract

The pyrano [3, 4-b] pyrrol-5-(1H)-ones 7 are stable cyclic analogues of pyrrole-2, 3- quinodimethane, and undergo Diels-Alder reaction with a range of acetylenes (dimethyl acetylenedicarboxylate, ethyl propiolate, ethyl trimethylsilylpropynoate, benzyne and the acetylene equivalent, phenyl vinyl sulfoxide), to give, after loss of carbon dioxide, indoles. The Diels-Alder reaction can be extended to the intramolecular variant to give cycloalka-[e ...