Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill
Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill
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DOI：
10.1080/15257770.2014.1001855
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发表时间：
2015-05-04
影响因子：
1.3
通讯作者：
Vyle, Joseph S.
中科院分区：
文献类型：
--
作者：
Cummings, Andrew J.;Ravalico, Francesco;Vyle, Joseph S.
使用5'-叠氮基-5'-脱氧胸苷和单-或双-N-炔丙基酰胺取代的偶氮苯之间的“点击”环加成反应制备了含有光可切换部分的新型核苷类似物。在溶液中，在稳定配体存在下使用 5mol% Cu(I) 可实现高定量产率。在不添加亚铜盐的情况下，通过在金属铜反应瓶中应用液体辅助研磨（LAG），也可以实现使用单炔丙酰胺的“点击”反应。具体而言，在乙酸乙酯存在下，使用 3/32('') (2.38mm) 直径铜球 (62mg) 在 60Hz 下进行过夜高速振动球磨 (HSVBM)，导致 5'-叠氮基核苷完全消耗，并干净地转化为相应的 1,3-三唑。
Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.