1,2,3-Triazoles as Leaving Groups: SNAr Reactions of 2,6-Bis-triazolyl Purines with O- and C-nucleophiles

Beilstein Journal of Organic Chemistry 2021
Dace Cīrule, Irina Novosjolova, Ērika Bizdēna, Māris Turks

A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.

Keywords
2,6-bistriazolyl purines, Nucleophilic aromatic substitution, Purine nucleosides, Triazoles
DOI
10.3762/BJOC.17.37
Hyperlink
https://www.beilstein-journals.org/bjoc/articles/17/37

Cīrule, D., Novosjolova, I., Bizdēna, Ē., Turks, M. 1,2,3-Triazoles as Leaving Groups: SNAr Reactions of 2,6-Bis-triazolyl Purines with O- and C-nucleophiles. Beilstein Journal of Organic Chemistry, 2021, Vol. 17, pp.410-419. ISSN 1860-5397. Available from: doi:10.3762/BJOC.17.37

Publication language
English (en)