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A study on chemical behaviors of some 4‐pyrones synthesized by one‐step reactions towards various amines
Author(s) -
Şener Ahmet,
Eskinoba Siddik,
Bildirici İshak,
Genç Hasan,
Kasimoǧullari Rahmi
Publication year - 2007
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.5570440209
Subject(s) - chemistry , ketene , medicinal chemistry , enol , cycloaddition , alkyl , ring (chemistry) , derivative (finance) , condensation reaction , pyrone , bicyclic molecule , stereochemistry , organic chemistry , catalysis , financial economics , economics
Cycloaddition of acetylbenzoyl ketene generated in situ as an intermediate during one‐step reaction between excess benzoylacetone and oxalylchloride to C=C double bond of cyclic enol form of benzoylacetone gave 3‐acetyl‐5‐benzoyl‐6‐methyl‐2‐phenyl‐4(4 H )‐pyrone 1a . Condensation reactions of 1a together with 3,5‐dibenzoyl‐2,6‐diphenyl‐4(4 H )‐pyrone 1b and 3‐benzoyl‐5‐ethoxycarbonyl‐2,6‐diphenyl‐4(4 H )‐pyrone 1c with two‐fold excess primary amines provided a series of 3‐benzoyl‐1‐alkyl‐5‐(1‐alkylimino‐ethyl)‐6‐phenyl‐2‐methyl‐4(1 H )‐pyridinone 2 , 3,5‐dibenzoyl‐1‐alkyl‐2,6‐diphenyl‐4(1 H )‐pyridinone 3a‐c and 3‐benzoyl‐1‐alkyl‐5‐ethoxycarbonyl‐2,6‐diphenyl‐4(1 H )‐pyridinone 3d,e derivatives, respectively. In addition, while prolonged reaction of n ‐pentylamine with unsymmetrical pyrone derivative 1a gives a symmetrical pyridinone derivative namely 3,5‐dibenzoyl‐2,6‐dimethyl‐1‐pentyl‐4(1 H )‐pyridinone 5 , much prolonged action n ‐pentylamine and then aqueous n ‐pentylamine on 1b resulted in degradation of the 4‐pyrone ring to give dibenzoylmethane.