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A study of some quinolizone derivatives
Author(s) -
AlJallo Hikmat N.,
AlAzawi Fatin W.
Publication year - 1973
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.5570100201
Subject(s) - chemistry , nitration , halogenation , decarboxylation , condensation , hydrolysis , organic chemistry , medicinal chemistry , catalysis , physics , thermodynamics
The condensation of methyl 2‐pyridylacetate and ethyl phenylpropiolate has been found to be a simple and convenient method for the preparation of 4‐quinolizone derivatives. Upon hydrolysis and decarboxylation, the initial condensation product, l‐carbethoxy‐2‐phenyl‐4H‐quinolizin‐4‐one (V) was converted to 2‐phenyl‐4 H ‐quinolizin‐4‐one (VII). Nitration and bromination of these quinolizones were affected under mild conditions. Nitration of V displaced the carbethoxy group, while bromination did not and 1,3‐dinitro‐4 H ‐quinolizin‐4‐one and 1‐carbeth‐oxy‐2‐phenyl‐3‐bromo‐4 H ‐quinolizin‐4‐one were obtained, respectively.