Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition |
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Authors: | Ugo Pradere Tamara R McBrayer Raymond F Schinazi Luigi A Agrofoglio |
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Institution: | a Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 6005, BP 6759, 45067 Orléans, France b Emory University School of Medicine, Atlanta, GA 30033, USA c Veterans Affairs Medical Center, Atlanta, GA 30033, USA |
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Abstract: | In this study, we described the synthesis of 1,4- and 1,5-disubstituted-1,2,3-triazolo-nucleosides from various alkynes with 1′-azido-2′,3′,5′-tri-O-acetylribose using either copper-catalyzed azide-alkyne cycloaddition (CuAAC) or ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC), respectively. Optimized RuAAC conditions were realized with the commercially available Cp∗RuCl(PPh3)2] under microwave heating, which allows a significant acceleration of the reaction times (from 6 h to 5 min). This reaction can work under water-containing system. RuAAC and CuAAC are useful tools for the synthesis of 1,2,3-triazolyl-nucleosides small libraries. |
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