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

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ŞENER A., Tozlu I., Genc H., Bildirici I., ARISOY K.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.44, no.5, pp.1077-1081, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 44 Issue: 5
  • Publication Date: 2007
  • Doi Number: 10.1002/jhet.5570440516
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1077-1081
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

1,5-Diphenyl-1H-pyrazole-3,4-(dicarboxylic acid-4-ethyl ester 2, obtained from the 4-ethoxycarbonyl-5phenyl-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 cyclo condensation reaction of 2 with hydrazine hydrate leads to the formation of pyrazolo[3,4d]pyridazine-4,7-dione 8, the reaction of 3 with anhydrous hydrazine provided a new bis pyrazole derivative 9.