Derivatives of 2,6-Diazidopurine and 2,6-Bis-(1,2,3-Triazol-1-yl) Purine as Useful Intermediates in the Synthesis of Modified Purine Nucleosides
16th Symposium on Chemistry of Nucleic Acid Components: Collection Symposium Series (M.Hocek, Ed.)
2014
Irina Novosjolova,
Ērika Bizdēna,
Māris Turks
Novel 2,6-bis-(1,2,3-triazol-1-yl)purine, N6-substituted-2-(1,2,3-triazol-1-yl)adenine and 6-alkyl/arylthio-2-(1,2,3-triazol-1-yl)purine and 2-alkylthio-6-(1,2,3-triazol-1-yl)purine nucleosides were synthesized. 2,6-Bis-(1,2,3-triazol-1-yl)purine nucleosides were obtained from 2,6-diazido compounds via copper (I) catalyzed azide-alkyne cycloaddition reactions. The bis-triazolyl derivatives appeared to be very reactive towards N- and S-nucleophiles. 2-Alkylthio-6-(1,2,3-triazol-1-yl)purine nucleosides were obtained in the reactions of 2,6-diazidopurines and thiols, and subsequent “click” reactions with terminal alkynes.
Keywords
purine nucleosides, bis-triazolyl derivatives, nucleophilic aromatic substitution
Novosjolova, I., Bizdēna, Ē., Turks, M. Derivatives of 2,6-Diazidopurine and 2,6-Bis-(1,2,3-Triazol-1-yl) Purine as Useful Intermediates in the Synthesis of Modified Purine Nucleosides. In: Collection Symposium Series. Vol.14. M.Hocek ed. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2014. pp.332-336. ISBN 978-80-86241-50-0.
Publication language
English (en)