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Synthesis of Important New Pyrrolo[3,4‐c]Pyrazoles and Pyrazolyl‐Pyrrolines from Heterocyclic β‐Ketonitriles
Author(s) -
Amer Fathy AbdelKader,
Hammouda Metwally,
ElAhl AbdelAziz Sayed,
AbdelWahab Bakr Fathy
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700217
Subject(s) - hydrazine (antidepressant) , chemistry , phenylhydrazine , hydrate , pyrazole , medicinal chemistry , organic chemistry , chromatography
Treatment of heterocyclic β‐ketonitriles 1a,b with hydrazine hydrate and phenylhydrazine afforded the hydrazine derivatives 2a‐d which cyclized in PPA into 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.