Kriķis Kārlis-Ēriks, Novosjolova Irina, Mishnev Anatoly, Turks Māris
Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia.
Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006, Riga, Latvia.
Beilstein J Org Chem. 2021 Jan 20;17:193-202. doi: 10.3762/bjoc.17.19. eCollection 2021.
A new method for C-N bond transformations into C-P bonds was developed using 1,2,3-triazoles as leaving groups in SAr-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 SAr-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-1-1,2,3-triazol-1-yl)-9-purin-6-yl)phosphonate.
开发了一种新方法，用于在SAr-Arbuzov反应中以1,2,3-三唑为离去基团将C-N键转化为C-P键。首次合成了一系列C6-膦酰化的2-三唑基嘌呤衍生物，在形成C-P键的反应中，分离产率高达82%。2,6-双三唑基嘌呤的SAr-Arbuzov反应遵循C6位对取代反应更具反应性的一般区域选择性模式，二乙基(9-庚基-2-(4-苯基-1H-1,2,3-三唑-1-基)-9H-嘌呤-6-基)膦酸酯的X射线分析明确证明了这一点。
