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Synthesis of 3‐Acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1 H )‐one Derivatives
Author(s) -
Nikam B. P.,
Kappe T.
Publication year - 2015
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.2030
Subject(s) - chemistry , potassium carbonate , medicinal chemistry , hydrochloride , hydroxylamine hydrochloride , anhydrous , hydroxylamine , ketone , organic chemistry , yield (engineering) , metallurgy , materials science
The cyclization of aryl ketone anilides 3 with diethyl malonate to affords 4‐hydroxy‐6‐phenyl‐6 H ‐pyrano[3,2‐ c ]‐pyridin‐2,5‐diones 4 in good yields. 3‐Acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1 H )‐ones 5 are obtained by ring‐opening reaction of 4‐hydroxy‐6‐phenyl‐6 H ‐pyrano[3,2‐ c ]‐pyridin‐2,5‐diones 4 in the presence of 1,2‐diethylene glycol. The reaction of 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1 H )‐ones 5 with hydroxylamine hydrochloride produces 4‐hydroxy‐3‐[ N ‐hydroxyethanimidoyl]‐1‐phenylpyridin‐2(1 H) ‐ones 6 from which 3‐alkyloxyiminoacetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1 H )‐ones 7 are obtained by reacting with alkyl bromides or iodides in the presence of anhydrous potassium carbonate with moderate yields. The similar compounds can be synthesized on refluxing 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1 H )‐ones 5 with substituted hydroxylamine hydrochloride in the presence of sodium bicarbonate with good yields. Most of the synthesized compounds are characterized by IR and NMR spectroscopic methods.