1,2,3-Triazoles as leaving groups in SNAr-Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

Kārlis-Ēriks Kriķis; Irina Novosjolova; Anatoly Mishnev; Māris Turks

doi:10.3762/bjoc.17.19

1,2,3-Triazoles as leaving groups in S_NAr-Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

Beilstein J Org Chem. 2021 Jan 20:17:193-202. doi: 10.3762/bjoc.17.19. eCollection 2021.

Authors

Kārlis-Ēriks Kriķis¹, Irina Novosjolova¹, Anatoly Mishnev², Māris Turks¹

Affiliations

¹ Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia.
² Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006, Riga, Latvia.

Abstract

A new method for C-N bond transformations into C-P bonds was developed using 1,2,3-triazoles as leaving groups in S_NAr-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 S_NAr-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: 2,6-bistriazolylpurines; Arbuzov reaction; nucleophilic aromatic substitution; purinylphosphonates.

Grants and funding

The authors thank the Latvian Council of Science for financial support (grant LZP-2018/2-0037).