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Studies on quinoline derivatives and related compounds. II. Synthesis of 5‐substituted 1‐ethyl‐1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylic acid
Author(s) -
Agui Hideo,
Komatsu Toshiaki,
Nakagome Takenari
Publication year - 1975
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.5570120324
Subject(s) - chemistry , quinoline , hydrolysis , ethyl ester , medicinal chemistry , nitro , antimicrobial , stereochemistry , organic chemistry , alkyl
The cyclization of m ‐substituted anilinomethylenemalonates ( 1 ) in the presence of polyphosphate ester and some other cyclizing agents gave mixtures of the isomeric ethyl 5‐ ( 2 ) and 7‐substituted 4‐hydroxy‐3‐quinolinecarboxylates ( 3 ), which led to mixtures of the corresponding quinolinecarboxylic acids ( 4 and 5 ) by hydrolysis. The proportions of 4 and 5 in the mixtures were determined on the basis of their nmr spectra. Novel 5‐chloro‐ ( 8a ), 5‐methyl‐ ( 8b ) and 5‐nitro‐1‐ethyl‐1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylic acids were prepared and evaluated for antimicrobial activities. No significant activity, however, was noted.