Cyclodextrin Methacrylate via Microwave-Assisted Click Reaction
Cyclodextrin Methacrylate via Microwave-Assisted Click Reaction
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DOI：
10.1021/ma8018975
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发表时间：
2008-12-23
期刊：
影响因子：
5.5
通讯作者：
Ritter, Helmut
中科院分区：
文献类型：
--
作者：
Munteanu, Maricica;Choi, SooWhan;Ritter, Helmut
甲基丙烯酸炔丙酯（1）与6 I-叠氮基-6 I-脱氧环麦芽七糖（2）进行点击反应，合成单-（1H-1，2，3-三唑-4-基）（甲基）2-甲基丙烯酰基-β-环糊精（3）。通过改变反应时间、温度曲线和铜催化剂来研究该过程。微波辐射与常规加热进行了比较。微波辅助Cu（I）催化的环加成反应使（2）在显著缩短的反应时间内完全转化为1，4-二取代三唑。在微波条件下，（2）与聚甲基丙烯酸炔丙酯（5）进行了高产率的环加成反应。通过使用NMR光谱评价了点击反应的区域选择性与反应条件的依赖性。在微波条件下进行的反应仅导致1，4-二取代的三唑，而常规加热导致区域异构体混合物。
Click reaction of propargyl methacrylate (1) with 6I-azido-6I-deoxycyclomaltoheptaose (2) was carried out to synthesize mono-(1H-1,2,3-triazol-4-yl)(methyl)2-methylacryl-beta-cyclodextrin (3). The process was investigated by varying the reaction time, temperature profiles, and copper catalyst. Microwave irradiation was compared with conventional heating. The microwave-assisted Cu(I)-catalyzed cycloaddition affords the complete conversion of (2) into 1,4-disubstituted triazole in a significant decreased reaction time. Under microwave conditions, the cycloaddition of (2) onto poly(propargyl methacrylate) (5) was conducted in excellent yields. The regioselectivity of click reactions in dependence of reaction conditions was evaluated by use of NMR spectroscopy. The reactions performed under microwave conditions led exclusively to 1,4-disubstituted triazole, while the conventional heating led to a regioisomeric mixture.