Synthesis of important new pyrrolo[3,4-c]pyrazoles and pyrazolyl-pyrrolines from heterocyclic β-ketonitriles

  • Fathy Abdel Kader Amer
  • , Metwally Hammouda
  • , Abdel Aziz Sayed El-Ahl
  • , Bakr Fathy Abdel-Wahab

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Treatment of heterocyclic β-ketonitriles 1a,b with hydrazine hydrate and phenylhydrazine afforded the hydrazine derivatives 2a-d which cyclized in PPAinto pyrrolo[3,4-c]pyrazoles 3a-d. Reaction of 1a,b with cyanoacetohydrazide furnished the cyanoacetyl pyrrolo[3,4-c]pyrazoles 4a,b. The hydrazine 2c reacted with β-diketone and β-ketoesters to afford pyrazolyl-pyrrolines 5-7. Also the later hydrazine reacted with some D-aldoses and aceteophenone to give the corresponding hydrazones 10-12 and hydrazine carboxamide derivatives 15a,b respectively.

Original languageEnglish
Pages (from-to)1543-1552
Number of pages10
JournalJournal of the Chinese Chemical Society
Volume54
Issue number6
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • 3-pyrrolidinone
  • Aceteophenone
  • Acetylacetone
  • D-aldoses
  • Ethyl acetoacetate
  • Hydrazine
  • Pyrrolo[3,4-c]pyrazole

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