Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines

Anton V. Dolzhenko, Anna V. Dolzhenko, Wai Keung Chui

Research output: Contribution to journalArticleResearchpeer-review

32 Citations (Scopus)

Abstract

A convenient and efficient synthesis of new 5-azapurine derivatives was developed. The regioisomeric 5-amino-6,7-dihydro- and 7-amino-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines were prepared in 3-4 steps from benzhydrazide via complementary and regiospecific routes as a part of our lead finding program. The molecular structures and tautomeric preferences of the compounds obtained were investigated using NMR spectral data and X-ray crystallography.

Original languageEnglish
Pages (from-to)12888-12895
Number of pages8
JournalTetrahedron
Volume63
Issue number52
DOIs
Publication statusPublished - 24 Dec 2007
Externally publishedYes

Keywords

  • 1,2,4-Triazoles
  • 5-Azapurines
  • Fused 1,3,5-triazines
  • Hydrazides
  • Tautomerism
  • Triazolotriazines

Cite this