Tetrahedron

Formation of enamine Schiff bases by ring cleavage of pyridine

RJ Molyneux, RY Wong

Index: Molyneux,R.J.; Wong,R.Y. Tetrahedron, 1977 , vol. 33, p. 1931 - 1934

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Citation Number: 3

Abstract

On treatment with diphenyldichloromethane or anisal chloride in the presence of acetone and aqueous sodium hydroxide, pyridine undergoes condensation and ring cleavage to yield the enamine Schiff bases 1, 1-diphenyl-2-azadeca-1, 3Z, 5Z, 7E-tetraen-9-one (1) and 1-(4-methoxyphenyl)-2-azadeca-1E, 3Z, 5Z, 7E-tetraen-9-one (7). The reaction proceeds through attack of acetonyl carbanion on the initially formed bis-pyridinium salt, followed by ...