A synthesis of new 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines via a selective three-component triazine ring annulation

Felicia Phei Lin Lim, Giuseppe Luna, Khai Ching Tan, Edward R.T. Tiekink, Anton V. Dolzhenko

Research output: Contribution to journalArticleResearchpeer-review

10 Citations (Scopus)

Abstract

3-Amino-substituted 5-aminopyrazoles were found to be suitable substrates for the synthesis of new 4-aminopyrazolo[1,5-a][1,3,5]triazines (5-aza-9-deaza-adenines) when used in the one-pot, three-component reaction with cyanamide and triethyl orthoformate under microwave irradiation. The reaction proceeded selectively and its scope was demonstrated by the preparation of a library of 4-aminopyrazolo[1,5-a][1,3,5]triazines. Some structural aspects of the prepared compounds were investigated using dynamic NMR spectroscopy and X-ray crystallography. The operational simplicity, short reaction time, and good reproducibility are attractive features of the developed robust and practical approach for the synthesis of 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines.

Original languageEnglish
Pages (from-to)2322-2329
Number of pages8
JournalTetrahedron
Volume75
Issue number15
DOIs
Publication statusPublished - 12 Apr 2019

Keywords

  • Aza-adenine
  • Azapurine
  • Microwave-assisted synthesis
  • Multicomponent reaction
  • One-pot synthesis
  • Pyrazole
  • Restricted rotation
  • Triazine

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