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The reaction of (chlorocarbonyl)phenyl ketene with enaminones: A novel synthesis of some 5-acyl-4-hydroxy-2-(1H)-pyridinones and 7-hydroxy-5-oxo-1,4-diazepin derivative

✍ Scribed by Mehdi Abaszadeh; Hassan Sheibani; Kazem Saidi

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 75 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.14

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✦ Synopsis

Abstract

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A series of substituted 5‐acyl‐4‐hydroxy‐2‐(1__H__)‐pyridinone derivatives has been prepared in a one‐step procedure from condensation of (chlorocarbonyl)phenyl ketene with some enaminones which were prepared from 1,3‐diketones, such as 2,4‐pentanedione, 1‐phenyl‐1,3‐butanedione, and ethyl acetoacetate in boiling toluene as a solvent. A mechanism is presented to account for the formation of the products. The overall sequence provides a simple and efficient route to prepare 3,4,5,6‐tetrasubstituted 2‐(1__H__)‐pyridinone in good to excellent yields and in a short experimental time. J. Heterocyclic Chem., (2009).

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