A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines

Felicia Phei Lin Lim, Nathan R. Halcovitch, Edward R.T. Tiekink, Anton V. Dolzhenko

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

A series of 5-aza-9-deaza- analogues of purine was effectively prepared using highly selective annulation of 1,3,5-triazine ring onto 5-aminopyrazole-4-carboxylates via a one-pot, multicomponent, microwave-assisted approach. The products were obtained in good yields and high purity. This catalyst-free method was demonstrated to be scalable and highly reproducible in different microwave reactors. Some structural features of the prepared compounds were studied in details using dynamic NMR spectroscopy and X-ray crystallography.

Original languageEnglish
Pages (from-to)1868-1879
Number of pages12
JournalTetrahedron
Volume74
Issue number15
DOIs
Publication statusPublished - 12 Apr 2018

Keywords

  • Dynamic NMR spectroscopy
  • Multicomponent reaction
  • Purine isostere
  • Pyrazole
  • Pyrazolo[1,5-a][1,3,5]triazine
  • Triazine

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