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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 367–373 | Cite as

A new method for the construction of [1,2,4]triazolo[1,5-a]pyridine system

  • Volodymyr A. Kovtunenko
  • Lyudmila M. PotikhaEmail author
  • Andriy V. Shelepyuk
  • Taras N. Tarasiuk
Article
  • 28 Downloads

Quaternization of 4-amino-4H-1,2,4-triazole with γ-bromodipnones and 5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one occurred at the N-1 nitrogen atom, with the formation of quaternary salts that were cyclized in the presence of bases into [1,2,4]triazolo[1,5-a]-pyridine derivatives. Quaternary 4-amino-4H-1,2,4-triazolium salts and aromatic 1-amino-1H-[1,2,4]triazolo[1,5-a]pyridinium salts can be deaminated by treatment with nitrous acid, giving 1-substituted 1,2,4-triazoles and the respective [1,2,4]triazolo[1,5-a]pyridines.

Keywords

4-amino-4H-1,2,4-triazole 1-amino-1H-[1,2,4]triazolo[1,5-a]pyridine γ-bromodipnone 5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one deamination quaternization 

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Volodymyr A. Kovtunenko
    • 1
  • Lyudmila M. Potikha
    • 1
    Email author
  • Andriy V. Shelepyuk
    • 2
  • Taras N. Tarasiuk
    • 1
  1. 1.Kyiv National Taras Shevchenko UniversityKyivUkraine
  2. 2.Enamine Ltd.KyivUkraine

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