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Issue 0, 1984
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The synthesis and chemistry of azolenines. Part 2. A general synthesis of pyrrole-2-carboxylic acid derivatives by the reaction of 2H-azirines with enamines, and the crystal and molecular structure of ethyl 3-phenyl-4,5,6,7-tetrahydroindole-2-carboxylate

Abstract

A new general synthesis of 1H-pyrrole-2-carboxylic acid derivatives is described. Reaction between appropriately substituted 2H-azirines and enamines gives a mixture of 2,3- and 3,4-dihydropyrroles, which on acid treatment yields the title compounds in moderate to high yields. Attempts to extend the reaction to the preparation of 2H- and 3N-pyrroles were unsuccessful; reasons are discussed. The crystal and molecular structure of ethyl 3-phenyl-4,5,6,7-tetrahydroindole-2-carboxylate has been determined. The molecules pack in highly coplanar, centrosymmetric, hydrogen-bonded pairs.

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J. Chem. Soc., Perkin Trans. 1, 1984, 111-118
Article type
Paper

The synthesis and chemistry of azolenines. Part 2. A general synthesis of pyrrole-2-carboxylic acid derivatives by the reaction of 2H-azirines with enamines, and the crystal and molecular structure of ethyl 3-phenyl-4,5,6,7-tetrahydroindole-2-carboxylate

K. W. Law, T. Lai, M. P. Sammes, A. R. Katritzky and T. C. W. Mak, J. Chem. Soc., Perkin Trans. 1, 1984, 111
DOI: 10.1039/P19840000111

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