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Synthesis and spectroscopic studies of some heterocyclic compounds. Reaction of 3‐aryl‐1‐phenyl‐2‐propen‐1‐ones with ethyl phenylacetate
Author(s) -
AlFarkh Yousuf A.,
AlHajjar Farouk H.,
Hamoud Hayat S.
Publication year - 1979
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.5570160101
Subject(s) - chemistry , phenylacetate , hydrate , aryl , hydrazine (antidepressant) , medicinal chemistry , sodium ethoxide , organic chemistry , ethyl formate , alkyl , biochemistry , ethanol , chromatography
3‐Aryl‐1‐phenyl‐2‐propen‐1‐one I reacted with ethyl phenylacetate (II) in the presence sodium ethoxide at room temperature to give the corresponding ethyl β‐aryl‐γ‐benzoyl‐α‐phenyl‐butyrate III. However,' when the same ketones were refluxed with ethyl phenylacetate, they gave the corresponding 4‐aryI‐3,6‐diphenyl‐3,4‐dihydro‐2 H ‐pyran‐2‐ones IV. The reactions of III and IV with hydrazine hydrate afforded the corresponding hydrazones VI and 2‐pyridones VIII, respectively. The structure and configuration of the products are based on chemical and spectroscopic evidence.