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1,4-Diacyl-3-acylamino-5-aryl-4,5-dihydro-1H-1,2,4-triazoles: Ring closure products of aromatic carbaldehyde (diaminomethylene) hydrazones with acylating agents

  • Z. Györgydeák
  • W. Holzer
  • R. W. Kunz
  • A. Linden
Organische Chemie Und Biochemie

Summary

Treatment of aromatic carbaldehyde (diaminomethylene)hydrazones1 with hot acetic anhydride or benzoyl chloride affords 1,4-diacyl-3-acylamino-5-aryl-4,5-dihydro-1H-1,2,4-triazoles2. In contrast, a new type of 0,N-acetal with an 1,2,4-triazole substructure (3) is obtained from 4-pyridine-carbaldehyde (diaminomethylene)hydrazone (li) by using a similar reaction procedure. The structures of all novel compounds were confirmed by spectroscopic data (1H and13C NMR, MS, IR); some representative compounds were also studied by X-ray analysis.

Keywords

1,2,4-Triazolines (Diaminomethylene)hydrazones X-Ray analysis NMR-spectroscopy 

1,4-Diacyl-3-acylamino-5-aryl-4,5-dihydro-1H-1,2,4-triazole: Ringschlußprodukte von aromatischen Aldehyd-dimethylaminomethylenhydrazonen mit Acylierungsmitteln

Zusammenfassung

Die Umsetzung von aromatischen Aldehyde-diaminomethylene-hydrazonen1 mit heißem Essigsäureanhydrid oder Benzoylchloride liefert 1,4-Diacyl-3-acylamino-5-aryl-4,5-dihydro-1H-1,2,4-triazole2. Im Gegensatz dazu erhält man aus 4-Pyridinaldehyd-diaminomethylenhydrazon (li) unter den gleichen Reaktionsbedingungen einen neuen O,N-Acetaltyp mit einer 1,2,4-Triazoleinheit. Die Struktur sämtlicher neuer Produkte wurde durch spektroskopische Daten (1H- und13C-NMR, MS, IR) unterstützt; einige repräsentative Vertreter wurden zusätzlich mittles Röntgenstrukturanalyse untersucht.

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Copyright information

© Springer-Verlag 1995

Authors and Affiliations

  • Z. Györgydeák
    • 1
  • W. Holzer
    • 2
  • R. W. Kunz
    • 3
  • A. Linden
    • 3
  1. 1.Kossuth Lajos Tudományegyetem Szerves Kémiai TanszékDebrecenHungary
  2. 2.Institut für Pharmazeutische Chemie der Universität WienWienAustria
  3. 3.Organisch-chemisches Institut der Universität ZürichZürichSwitzerland

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