Functionalization of 2H-1,2,3-Triazole C-Nucleoside Template via N2 Selective Arylation
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- 作者：Alexandra Basilio Lopes ; Patrick Wagner ; Rodrigo Octavio Mendonça Alves de Souza ; Nadège Lubin Germain ; Jacques Uziel ; Jean-Jacques Bourguignon ; Martine Schmitt ; Leandro S. M. Miranda
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：June 3, 2016
- 年：2016
- 卷：81
- 期：11
- 页码：4540-4549
- 全文大小：485K
- 年卷期：0
- ISSN：1520-6904
文摘
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<sup>2sup>-Aryl-1,2,3-triazole C-nucleoside compounds that could be obtained by selective 1,2,3-triazole heterocycle N<sup>2sup> arylation in 1-β-<span class="smallcaps">dspan>-ribofuranosyl-2H-1,2,3-triazole substrate were designed in this study. The optimized condition used AdBrettPhos/[PdCl(allyl)]<sub>2sub> 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.