A NEW METHOD FOR THE CONSTRUCTION OF [1,2,4]TRIAZOLO[1,5-<i>a</i>]PYRIDINE SYSTEM

Authors

  • Владимир А. Ковтуненко Kyiv National Taras Shevchenko University, 64 Volodymyrska St., Kyiv 01033
  • Людмила М. Потиха Kyiv National Taras Shevchenko University, 64 Volodymyrska St., Kyiv 01033
  • Андрей В. Шелепюк Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660
  • Тараc H. Тарасюк Kyiv National Taras Shevchenko University, 64 Volodymyrska St., Kyiv 01033

DOI:

https://doi.org/10.1007/5011

Keywords:

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

Abstract

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.

Authors: Volodymyr A. Kovtunenko, Lyudmila M. Potikha*, Andriy V. Shelepyuk, Taras N. Tarasiuk

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Published

2019-05-22

Issue

Vol. 55 No. 4/5 (2019): In memory of Professor Valerii Dmitrievich Orlov

Section

Original Papers