1,2,3-Triazoles as Leaving Groups in SNAr-Arbuzov Reactions: Synthesis of C6-Phosphonated Purine Derivatives

Beilstein Journal of Organic Chemistry 2021
Kārlis Ēriks Kriķis, Irina Novosjolova, Anatolijs Mišņovs, Māris Turks

A new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming event. The SNAr–Arbuzov reaction of 2,6-bistriazolylpurines follows the general regioselectivity pattern of the C6-position being more reactive towards substitution, which was unambiguously proved by X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate.

Keywords
Arbuzov reaction; 2,6-bistriazolylpurines; nucleophilic aromatic substitution; purinylphosphonates
DOI
10.3762/BJOC.17.19
Hyperlink
https://www.beilstein-journals.org/bjoc/articles/17/19

Kriķis, K., Novosjolova, I., Mišņovs, A., Turks, M. 1,2,3-Triazoles as Leaving Groups in SNAr-Arbuzov Reactions: Synthesis of C6-Phosphonated Purine Derivatives. Beilstein Journal of Organic Chemistry, 2021, Vol. 17, pp.193-202. ISSN 1860-5397. Available from: doi:10.3762/BJOC.17.19

Publication language
English (en)