title: Functionalization of 2H-1,2,3-Triazole C-Nucleoside Template via N(2) Selective Arylation.
abstract: 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.
authors.affiliation: 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.
authors.forename: Alexandra Basilio
authors.initials: AB
authors.lastname: Lopes
authors.affiliation: Laboratoire d'Innovation Thérapeutique UMR7200, Faculté de Pharmacie, Université de Strasbourg, CNRS , 74 route du Rhin, BP60024 Illkirch, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Wagner
authors.affiliation: 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.
authors.forename: Rodrigo Octavio Mendonça Alves
authors.initials: RO
authors.lastname: de Souza
authors.affiliation: Université de Cergy-Pontoise, UMR CNRS 8123 , Laboratoire de chimie biologique EA 4505, F-95000 Cergy-Pontoise Cedex, France.
authors.forename: Nadège Lubin
authors.initials: NL
authors.lastname: Germain
authors.affiliation: Université de Cergy-Pontoise, UMR CNRS 8123 , Laboratoire de chimie biologique EA 4505, F-95000 Cergy-Pontoise Cedex, France.
authors.forename: Jacques
authors.initials: J
authors.lastname: Uziel
authors.affiliation: Laboratoire d'Innovation Thérapeutique UMR7200, Faculté de Pharmacie, Université de Strasbourg, CNRS , 74 route du Rhin, BP60024 Illkirch, France.
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Bourguignon
authors.affiliation: Laboratoire d'Innovation Thérapeutique UMR7200, Faculté de Pharmacie, Université de Strasbourg, CNRS , 74 route du Rhin, BP60024 Illkirch, France.
authors.forename: Martine
authors.initials: M
authors.lastname: Schmitt
authors.affiliation: 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.
authors.forename: Leandro S M
authors.initials: LS
authors.lastname: Miranda