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Reactions of α,β‐unsaturated ketones with cyanoacetamide
Author(s) -
AlHajjar Farouk H.,
Jarrar Adil A.
Publication year - 1980
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.5570170733
Subject(s) - chemistry , cyanoacetamide , sodium ethoxide , piperidine , aryl , medicinal chemistry , organic chemistry , ethanol , alkyl
Abstract 3‐Aryl‐1‐phenyl‐2‐propen‐1‐ones Ia‐f and aroylphenylacetylenes Va‐d reacted under reflux for 3 hours with cyanoacetamide in the presence of sodium ethoxide to give the corresponding 4‐aryl‐3‐cyano‐6‐phenyl‐2‐(1 H )pyridones VI. However, when ketones Ia‐e were refluxed with cyanoacetamide for one hour in the presence of sodium ethoxide or piperidine, they gave the corresponding 4‐aryl‐3‐cyano‐3,4‐dihydro‐6‐phenyl‐2‐(1 H )pyridones IIIa‐e, which upon heating with selenium gave the corresponding 2‐pyridones VI. The structures of the products are based on chemical and spectroscopic evidence.