A Novel Synthesis of N-Styryl Heterocycles

Reaction of the anions of a variety of 2-carboethoxy N-heterocycles with styrene oxide yields directly the N-(trans-2-styryl)-2-carboxylic acids. The reaction has been shown to proceed through a lactone intermediate which undergoes rapid elimination to form the unsaturated acid. The reaction has bee...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 51; no. 22; pp. 3765 - 3770
Main Authors Rokach, J, Girard, Y, Atkinson, J. G
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 15.11.1973
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Summary:Reaction of the anions of a variety of 2-carboethoxy N-heterocycles with styrene oxide yields directly the N-(trans-2-styryl)-2-carboxylic acids. The reaction has been shown to proceed through a lactone intermediate which undergoes rapid elimination to form the unsaturated acid. The reaction has been used to alkylate 2-carboethoxy pyrrole, diethyl pyrazole-3,5-dicarboxylate, ethyl indole-2-carboxylate, ethyl benzimidazole-2-carboxylate, and ethyl 2-pyrrolidone-5-carboxylate. Yields were 82, 88, 93.5, 57, and 5% respectively.1-(trans-2-Styryl)benzirnidazole-2-carboxylic acid of m.p. 75-77 °C undergoes an interesting, reversible solid-state transformation to a high melting (255-260 °C), presumably zwitterionic, form.
ISSN:0008-4042
1480-3291
DOI:10.1139/v73-562