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Convenient preparative methods for N ‐aryl‐γ‐pyridones from γ‐pyrones
Author(s) -
Looker James H.,
Cliffton Michael D.
Publication year - 1986
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.5570230102
Subject(s) - chemistry , aniline , hydrochloride , hydrochloric acid , aqueous solution , aryl , yield (engineering) , amine gas treating , hydroxymethyl , organic chemistry , medicinal chemistry , alkyl , materials science , metallurgy
Abstract 2‐Hydroxymethyl‐5‐methoxy‐4‐ H ‐pyran‐4‐one ( 1 ) reacts with aniline and six aniline derivatives in very dilute aqueous hydrochloric acid at reflux temperature to give the N ‐aryl‐γ‐pyridone. A second procedure utilizes the aromatic amine hydrochloride by reacting it with 1 in aqueous medium at reflux temperature. p‐N itroaniline hydrochloride and 1 give the N ‐aryl‐γ‐pyridone in 65% yield, as opposed to 12% from the dilute acid procedure.