Synthesis and some reactions of 4-(ethoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carboxylic acid

1,5‐Diphenyl‐1H‐pyrazole‐3,4‐dicarboxylic acid‐4‐ethyl ester 2, obtained from the 4‐ethoxycarbonyl‐5‐phenyl‐2,3‐furandione 1 and N‐benzylidene‐N′‐phenyl hydrazine, was converted via reactions of its acid chloride 3 with various alcohols or N‐nucleophiles into the corresponding ester 5 or amide deriv...

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Veröffentlicht in:Journal of heterocyclic chemistry 2007-09, Vol.44 (5), p.1077-1081
Hauptverfasser: Şener, Ahmet, Bildirici, İshak, Tozlu, İsrafil, Genç, Hasan, Arısoy, Kadir
Format: Artikel
Sprache:eng
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Zusammenfassung:1,5‐Diphenyl‐1H‐pyrazole‐3,4‐dicarboxylic acid‐4‐ethyl ester 2, obtained from the 4‐ethoxycarbonyl‐5‐phenyl‐2,3‐furandione 1 and N‐benzylidene‐N′‐phenyl hydrazine, was converted via reactions of its acid chloride 3 with various alcohols or N‐nucleophiles into the corresponding ester 5 or amide derivatives 6, respectively. In addition, 2 was decarboxylated to give ethyl 1,5‐diphenylpyrazole‐4‐carboxylate 4. Nitrile 7 derivative of 2 was also obtained by dehydration of 6a in a mixture of SOCl2 and DMF. While cyclocondensation reaction of 2 with hydrazine hydrate leads to the formation of pyrazolo[3,4‐d]pyridazine‐4,7‐dione 8, the reaction of 3 with anhydrous hydrazine provided a new bis pyrazole derivative 9.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570440516