Toward Unsymmetrical 2,6-Bistriazolylpurine Nucleosides

Chemistry of Heterocyclic Compounds 2021
Dace Cīrule, Irina Novosjolova, Andrejs Spuris, Anatolijs Mišņovs, Ērika Bizdēna, Māris Turks

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.

Keywords
2,6-bistriazolylpurines, purine nucleosides, triazoles, nucleophilic aromatic substitution
DOI
10.1007/s10593-021-02906-6
Hyperlink
https://link.springer.com/article/10.1007%2Fs10593-021-02906-6

Cīrule, D., Novosjolova, I., Spuris, A., Mišņovs, A., Bizdēna, Ē., Turks, M. Toward Unsymmetrical 2,6-Bistriazolylpurine Nucleosides. Chemistry of Heterocyclic Compounds, 2021, Vol. 57, No. 3, pp.292-297. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-021-02906-6

Publication language
English (en)