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TOWARD UNSYMMETRICAL 2,6-BISTRIAZOLYLPURINE NUCLEOSIDES

Dace Cīrule, Irina Novosjolova, Andrejs Spuris, Anatoly Mishnev, Ērika Bizdēna, Māris Turks
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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.

Keywords


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

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