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Studies on quinoline derivatives and related compounds. IV. Synthesis of 4‐substituted 1‐alkyl‐1,4‐dihydro‐3‐quinolinecarboxylic acid
Author(s) -
Agui Hideo,
Nakagome Takenari
Publication year - 1976
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.5570130416
Subject(s) - chemistry , alkylation , hydrolysis , alkyl , iodide , medicinal chemistry , quinoline , methylenedioxy , acid hydrolysis , organic chemistry , alkoxy group , catalysis
Abstract By the displacement reactions of 1‐ethyl‐4‐chloro‐3‐carboethoxy‐6,7‐methylenedioxyquinolinium iodide ( 3a ), several 4‐substituted derivatives including the 4‐thioxo ( 1c ) and 4‐amino derivatives ( 6 ) of oxolinic acid were prepared. The acid 1c and its N 1 ‐substituted derivatives ( 18a‐h ) were prepared alternatively by alkylation of ethyl 4‐ethylmercapto‐6,7‐methylenedioxy‐3‐quinolinecarboxylate ( 15 ) followed by treatment with sodium hydrosulfide and hydrolysis.