Studies on quinoline derivatives and related compounds. VI. A novel displacement reaction of 1‐ethylquinolinium iodides with nucleophiles | Zendy

Agui Hideo | Zendy; Nakagome Takenari | Zendy

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Studies on quinoline derivatives and related compounds. VI. A novel displacement reaction of 1‐ethylquinolinium iodides with nucleophiles

Author(s) -

Agui Hideo,

Nakagome Takenari

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.5570160713

Subject(s) - chemistry , nucleophile , ethyl iodide , reagent , quinoline , iodide , hydrolysis , methylenedioxy , medicinal chemistry , single displacement reaction , alkaline hydrolysis , ethyl ester , ethyl benzoate , acid hydrolysis , organic chemistry , catalysis , alkyl , halogen

The reaction of 4‐amino‐ ( 3a ) and 4‐anilino‐3‐carbethoxy‐1‐ethyl‐6,7‐methylenedioxy‐quinolinium iodide ( 3b ) with nucleophilic reagents produced 7‐substituted 4‐amino‐3‐carboxy‐1‐ethyl‐6‐hydroxyquinolinium betaines ( 5b‐d ) and 7‐substituted 1‐ethyl‐1,4‐dihydro‐6‐hydroxy‐4‐phenylimino‐3‐quinolinecarboxylic acid ( 6b‐d ), respectively, which led to 7‐substituted 1‐ethyl‐1,4‐dihydro‐6‐hydroxy‐4‐oxo‐3‐quinolinecarboxylic acids ( 1b‐d ) by alkaline hydrolysis. With a variety of 1‐ethyl‐1,4‐dihydroquinoline carboxylates ( 16a‐e ) these novel displacement reactions were attempted.

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