TOWARD UNSYMMETRICAL 2,6-BISTRIAZOLYLPURINE NUCLEOSIDES

Authors

  • Dace Cīrule Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Irina Novosjolova Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Andrejs Spuris Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia Riga State Gymnasium No. 1, 8 Raiņa Blvd., Riga LV-1050, Latvia
  • Anatoly Mishnev Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Ērika Bizdēna Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Māris Turks Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia

DOI:

https://doi.org/10.1007/6065

Keywords:

2, 6-bistriazolylpurines, purine nucleosides, triazoles, nucleophilic aromatic substitution.

Abstract

Synthetic routes toward purine derivatives containing two different 1,2,3-triazolyl substituents at their C-2 and C-6 positions were developed. 2,6-Bistriazolylpurines containing electron-withdrawing substituents in their triazole rings undergo C-6-selective SNAr reactions with other triazoles or NaN3. In the latter case, a CuAAC reaction provides differently substituted 2,6-bistriazolylpurines. Also a general synthetic sequence toward the title compounds regardless of their electronic character was developed. It makes a use of 6-amino-2-azidopurine derivatives, which are obtained by C-6-selective reduction of 2,6-diazidopurines.

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Published

2021-03-15

Issue

Vol. 57 No. 3 (2021)

Section

Original Papers