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A convenient synthesis of 5‐acyl‐6‐substituted 3‐cyano‐2(1 H )‐pyridinones
Author(s) -
Jones Winton D.,
Schnettler Richard A.,
Huber Edward W.
Publication year - 1990
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.5570270307
Subject(s) - cyanoacetamide , chemistry , synthon , dimethylformamide , acetal , structural isomer , hydrolysis , diketone , organic chemistry , aryl , medicinal chemistry , alkyl , solvent
2‐Dimethylaminomethylidene‐1,3‐diketones are useful synthons for the construction of 5‐acyl‐6‐substituted‐3‐cyano‐2(1 H )‐pyridinones. The reaction of these 1,3‐diketones and the anion of cyanoacetamide gave the title compounds. When the 1,3 diketone contained different alkyl or aryl groups, mixtures of regioisomers were formed. To circumvent this problem, dimethylaminomethylidene hydrazones, regioselectively prepared from dimethylhydrazino enones and dimethylformamide dimethyl acetal were reacted with cyanoacetamide anion followed by acid hydrolysis to give the title compounds.