Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

Jānis Miķelis Zaķis, Kristers Ozols, Irina Novosjolova, Reinis Vilšķērsts, Anatoly Mishnev, Māris Turks (Coresponding Author)

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of SNAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including 15N NMR.

Original languageEnglish
Pages (from-to)4753-4771
Number of pages19
JournalJournal of Organic Chemistry
Volume85
Issue number7
DOIs
Publication statusPublished - 3 Apr 2020

Field of Science*

  • 1.4 Chemical sciences
  • 3.1 Basic medicine

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

Fingerprint

Dive into the research topics of 'Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives'. Together they form a unique fingerprint.

Cite this