Premium
The synthesis of a pyrido[2,3‐ c ]pyridazine: A cinnoline related to 6‐fluoronalidixic acid
Author(s) -
Sanchez Joseph P.,
Trehan Ashok K.,
Nichols Jeffry B.
Publication year - 1987
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.5570240112
Subject(s) - pyridazine , chemistry , ring (chemistry) , cinnoline , nalidixic acid , medicinal chemistry , hydrazine (antidepressant) , diazo , stereochemistry , organic chemistry , antibiotics , biochemistry , antibiotic resistance , chromatography
An analog of the pyrido[2,3‐ c ]pyridazine ring system, 1‐ethyl‐6‐fluoro‐1,4‐dihydro‐7‐methyl‐4‐oxopyrido‐[2,3‐ c ]pyridazine‐3‐carboxylic acid ( 13 ), related to both Cinoxacin ( 1 ) and nalidixic acid ( 2 ), has been synthesized. The reductive ring closure of 2‐chloro‐α‐diazo‐6‐methyl‐5‐nitro‐β‐oxo‐3‐pyridinepropanoic acid, ethyl ester ( 7 ), proved to be the key reaction providing entry into the ring system.