通过铜和钌催化的叠氮化物-炔烃1,3-偶极环加成反应制备利巴韦林类似物。
Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition.
作者信息
Pradere Ugo, Roy Vincent, McBrayer Tamara R, Schinazi Raymond F, Agrofoglio Luigi A
机构信息
Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 6005, BP 6759, 45067 Orléans, France.
Emory University School of Medicine, Atlanta, GA 30033, USA.
出版信息
Tetrahedron. 2008 Sep 15;64(38):9044-9051. doi: 10.1016/j.tet.2008.07.007. Epub 2008 Jul 5.
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--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(PPh)] 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.
摘要
在本研究中，我们分别描述了使用铜催化的叠氮化物-炔烃环加成反应（CuAAC）或钌催化的叠氮化物-炔烃环加成反应（RuAAC），由各种炔烃与1'-叠氮基-2',3',5'-三乙酰核糖合成1,4-和1,5-二取代的1,2,3-三唑并核苷。在微波加热条件下，使用市售的[Cp*RuCl(PPh)]实现了RuAAC反应条件的优化，这使得反应时间大幅缩短（从6小时缩短至5分钟）。该反应可在含水体系中进行。RuAAC和CuAAC是合成1,2,3-三唑基核苷小型文库的有用工具。
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