Biocatalysis and Organic Synthesis Group, Universidade Federal do Rio de Janeiro , Av Athos da Silveira Ramos 149, Centro de Tecnologia, Bl A, 21941909 Ilha do Fundão, Rio de Janeiro, Brazil.
Laboratoire d'Innovation Thérapeutique UMR7200, Faculté de Pharmacie, Université de Strasbourg, CNRS , 74 route du Rhin, BP60024 Illkirch, France.
J Org Chem. 2016 Jun 3;81(11):4540-9. doi: 10.1021/acs.joc.6b00323. Epub 2016 May 18.
C-Nucleosides are an underexplored and important class of nucleosides with antiviral and anticancer activity. In addition, triazole heterocycles are well employed as a strategy to modify nucleobase in nucleoside analogues, although rare examples were described for triazoyl C-nucleosides. N(2)-Aryl-1,2,3-triazole C-nucleoside compounds that could be obtained by selective 1,2,3-triazole heterocycle N(2) arylation in 1-β-d-ribofuranosyl-2H-1,2,3-triazole substrate were designed in this study. The optimized condition used AdBrettPhos/[PdCl(allyl)]2 as the catalyst system. This transformation was accomplished by aryl halides bearing an electron donor and withdrawing groups, as well as by heterocyclic halides in good to excellent yields. The transformation developed in this study represents a significant contribution to the nucleoside field, once it allows for the synthesis of unexplored scaffolds through selective functionalization of triazole nucleosides.
C-核苷是一类未充分探索的重要核苷，具有抗病毒和抗癌活性。此外，三唑杂环被很好地用作修饰核苷类似物中碱基的策略，尽管三唑 C-核苷的例子很少。本研究设计了可通过在 1-β-D-呋喃核糖基-2H-1,2,3-三唑底物中选择性 1,2,3-三唑杂环 N(2)芳基化得到的 N(2)-芳基-1,2,3-三唑 C-核苷化合物。优化条件采用 AdBrettPhos/[PdCl(allyl)]2 作为催化剂体系。该转化可通过带有给电子和吸电子基团的芳基卤化物以及杂环卤化物进行，产率良好至优秀。本研究中开发的转化为核苷领域做出了重要贡献，因为它允许通过三唑核苷的选择性官能化来合成未探索的支架。
