Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene
作者:James T. Fletcher、Sara E. Walz、Matthew E. Keeney
DOI:10.1016/j.tetlet.2008.09.136
日期:2008.12
Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal
已经开发了两步一锅法反应条件来合成1-取代的1,2,3,3-三唑。该转化涉及在水性反应条件下,碱催化的三甲基甲硅烷基乙炔的脱保护,然后是铜催化的惠斯根1,3-偶极环加成。以碳酸钾为碱,以甲醇为醇性水性助溶剂,可得到所需产物的最佳收率。发现该反应条件对于烷基和芳基叠氮化物反应物都是成功的,包括具有给电子和吸电子功能的类似物。该方法是简单且区域选择性的方法,通过该方法可以直接从叠氮化物前体制备1-取代的1,2,3-三唑化合物。