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The reaction of (chlorocarbonyl)phenyl ketene with enaminones: A novel synthesis of some 5‐acyl‐4‐hydroxy‐2‐(1 H )‐pyridinones and 7‐hydroxy‐5‐oxo‐1,4‐diazepin derivative
Author(s) -
Abaszadeh Mehdi,
Sheibani Hassan,
Saidi Kazem
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.14
Subject(s) - chemistry , ketene , ethyl acetoacetate , toluene , derivative (finance) , organic chemistry , ketone , solvent , condensation , boiling , medicinal chemistry , combinatorial chemistry , catalysis , financial economics , economics , physics , thermodynamics
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).