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Studies on the reactions of cyclic oxalyl compounds with hydrazines or hydrazones : Synthesis and reactions of 4‐benzoyl‐1‐(3‐nitrophenyl)‐5‐phenyl‐1 H ‐pyrazole‐3‐carboxylic acid
Author(s) -
Şener Ahmet,
Kasim Şener M.,
Bildmci Ishak,
Kasimogullari Rahmi,
Akçamur Yunus
Publication year - 2002
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.5570390503
Subject(s) - chemistry , pyrazole , hydrazine (antidepressant) , pyridazine , medicinal chemistry , carboxylic acid , amide , organic chemistry , hydrate , formic acid , nitrile , hydrazone , oxalyl chloride , hydroxylamine , chromatography
The 1 H ‐pyrazole‐3‐carboxylic acid 2 , obtained from the furan‐2,3‐dione 1 and N ‐Benzylidene‐ N '‐(3‐nitrophenyl) hydrazine, was converted via reactions of its acid chloride 3 with various alcohols or N‐nucleo‐philes into the corresponding ester or amide derivatives 4 or 5 , respectively. Nitrile 6 and anilino‐pyrazole acid 7 derivatives of 2 were also obtained by dehydration of 5a in a mixture of SOCl 2 with DMF and reduction of 2 with sodium polysulphide, respectively. While cyclocondensation reactions of 2 or 7 with phenyl hydrazine or hydrazine hydrate and 6 with only anhydrous hydrazine lead to derivatives of pyrazolo[3,4‐ d ]‐pyridazinone 8 and pyrazolo[3,4‐ d ]pyridazine amine 9 , respectivel. The reaction of 2 with 2‐hydrazinopyri‐dine provided hydrazono‐pyrazole acid derivative 10 , which was decarboxylated to give hydrazono‐pyra‐zole derivative 11 . Pyrazolo[4,3‐ d ]oxazinone 12 and 2‐quinolyl pyrazolo[3,4‐ d ]pyridazine 13 derivatives were also prepared by cyclocondensation reactions of 2 with hydroxylamine hydrochloride and 7 with acetaldehyde, respectively.