Monatshefte für Chemie / Chemical Monthly

, Volume 121, Issue 12, pp 1023–1030 | Cite as

Studies in the Vilsmeier-Haack reaction, part VII: Synthesis and reaction of 3-methyl-1-phenyl-4-acetyl hydrazono 2-pyrazoline-5-one(-5-thione)

  • Ibrahim M. A. Awad
Organische Chemie Und Biochemie
Received:
Revised:
Accepted:

Summary

The keto (thio) tautomers1–4 of the hydrazono pyrazolone, thiopyrazolone derivatives underwent simultaneous diformylation, chlorination (desulphurization) and ring closure under Vilsmeier reaction conditions giving the pyrazolo[3,4-c]pyrazole aminoacroleins (5,6). Treatment of5 and/or6 with proper reagents afforded the corresponding pyrazolo[3,4-c]pyrazoles with different heterocyclic systems at the 3-position.

The structures of these compounds were confirmed by elemental analysis, IR and1H-NMR spectroscopy. All synthesized compounds have been screened in vitro for their antibacterial activities against a number of Gram-positive and Gram-negative bacteria.

Keywords

Hydrazono-5-chloro pyrazole Pyrazolo[3,4-c]pyrazole Isoxazolylpyrazolo[3,4-c]-pyrazole Pyrazolylpyrazolo[3,4-c]pyrazole Physiological activity 

Untersuchungen zur Vilsmeier-Haack Reaktion, 7. Mitt.: Synthese und Reaktionen von 3-Methyl-1-phenyl-4-acetylhydrazono-2-pyrazolin-5-on(-5-thion)

Zusammenfassung

Die Keto-(Thio)-Tautomeren1–4 der Hydrazonopyrazolon-/Thiopyrazolon-Derivate gingen unter Vilsmeier-Bedingungen zugleich Diformylierung, Chlorierung (Entschwefelung) und Ringschluß zu Pyrazolo[3,4-c]pyrazol-aminoacroleinen5 und6 ein. Aus5 und/oder6 konnten die entsprechenden Pyrazolo[3,4-c]pyrazole mit verschiedenen heterocyclischen Systemen in 3-Position erhalten werden. Die Strukturen der Verbindungen wurden mittels Elementaranalyse, IR und1H-NMR überprüft. Alle synthetisierten Verbindungen wurden in vitro bezüglich ihrer antibakteriellen Aktivität gegenüber einer Anzahl Gram-positiver und Gram-negativer Bakterien untersucht.

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Copyright information

© Springer-Verlag 1990

Authors and Affiliations

  • Ibrahim M. A. Awad
    • 1
  1. 1.Chemistry Department, Faculty of ScienceAssiut UniversityAssiutEgypt

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