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Construction of 5,6-Ring-Fused 2-Pyridones: An Effective Annulation Tactic Achieved in Water

Amos B. Smith, III*, Onur Atasoylu, Douglas C. Beshore

*Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, USA, Email: smithabsas.upenn.edu

A. B. Smith, III, O. Atasoylu, D. C. Beshore, Synlett, 2009, 2643-2646.

DOI: 10.1055/s-0029-1217749 (free Supporting Information)


Abstract

A tandem condensation of propiolamide and cyclic β-keto methyl esters in water, followed by acid- or base-promoted intramolecular ring closure and decarboxylation enables an efficient synthesis of a  5,6-fused 2-pyridone ring system.

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Key Words

heterocycles, 2-pyridones, active methylenes, condensation, fused-ring systems, tandem reactions, Michael additions, green chemistry


ID: J60-Y2009-2830