Studies on quinoline derivatives and related compounds. IV. Synthesis of 4‐substituted 1‐alkyl‐1,4‐dihydro‐3‐quinolinecarboxylic acid | Zendy

Agui Hideo | Zendy; Nakagome Takenari | Zendy

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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

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.

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