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Communication | Regular issue | Vol 23, No. 5, 1985, pp.1073-1076
Published online, 1st January, 1970
DOI: 10.3987/R-1985-05-1073
Acid-catalyzed Cyclization of 2-Hydroxy-3-pyrrolone Derivatives. 2-Methoxy-3(2H)-furanones as Precursors of Polycyclic Nitrogen Heterocycles

Jeremiah P. Freeman* and Mary Kay Fettes-Fields

*Department of Chemistry, University of Oregon, Eugene, OR 97403, U.S.A.

Abstract

Condensation of 2-methoxy-3(2H)-furanones with β-substituted ethylamines followed by treatment with various acid catalysts gives rise to polycyclic nitrogen heterocycles by way of two intramolecular cyclizations. The pathway depends upon the nature of the β-substituent. β-Aryl substituents underwent alkylation through the 2-position of the hetero ring while β-amino- and β-thio groups cyclized to the 5-position.