Arylthiols in SNAr Reactions with 2,6-Diazidopurine Derivatives
Paul Walden 11th Symposium on Organic Chemistry: Program and Abstract Book 2019
Andris Jeminejs, Ērika Bizdēna, Irina Novosjolova

Purine and thiopurine derivatives are widely studied due to their broad spectrum of biological activity. Some of them have already been used as an effective tool in the treatment of cancer and autoimmune disorders. 2,6-Diazidopurine substrate has been proven to be a valuable starting material in the synthesis of new arylthiopurine derivatives. Nucleophilic substitution with thiophenols can be mainly observed at C2 position of purine, providing 2-arylthio-6-azidopurine derivatives with yields. In solution these compounds exist in azide-tetrazole equilibrium which is dependent on several factors, such as temperature, solvent polarity and substituent electron donating properties. Further CuAAC reaction and different sequence of the reactions leaded to 2-arylthio-6 triazolyl- and 6-arylthio-2-triazolylpurine derivatives. Despite the location of triazolyl- and thiogroups following nucleophilic substitution with piperidine was observed regioselectively at C6 position of purine.


Atslēgas vārdi
Purine derivatives, thiopurines, thophenols, nucleophilic substitution

Jeminejs, A., Bizdēna, Ē., Novosjolova, I. Arylthiols in SNAr Reactions with 2,6-Diazidopurine Derivatives. No: Paul Walden 11th Symposium on Organic Chemistry: Program and Abstract Book, Latvija, Rīga, 19.-20. septembris, 2019. Rīga: 2019, 45.-45.lpp.

Publikācijas valoda
English (en)
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