黄原酸酯参与的芳杂环分子间自由基烷基化研究  

Intermolecular Radical Alkylation of Aromatic Heterocycles Using Xanthates

作　　者：郦勇 邹良邦 田凯迪 蔡婷娜 LI Yong;ZOU Liangbang;TIAN Kaidi;CAI Tingna(Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process,Shaoxing University,Shaoxing,Zhejiang 312000)

机构地区：[1]绍兴文理学院浙江省精细化学品传统工艺替代技术研究实验室,浙江绍兴312000

出　　处：《绍兴文理学院学报》2023年第8期85-96,共12页Journal of Shaoxing University

基　　金：国家自然科学基金项目“Stemmadenine类型生物碱及其生源衍生天然产物Arborisidine的不对称合成研究”(21801167);浙江省自然科学基金项目“新环系一叶萩碱Virosinine A和类似物的全合成研究”(LQ17B020002).

摘　　要：芳杂环是药物分子中的重要骨架,而自由基烷基化是修饰芳杂环的有效手段之一.综述了2003年以来报道的黄原酸酯参与的芳杂环分子间自由基烷基化反应.黄原酸酯化合物可以在较高温度下被过氧月桂酰等过氧化物引发,亦可以在较低温度下被三烷基硼/氧气或者在光敏分子的介导下被可见光引发.生成的烷基自由基可以与吡咯、吲哚、苯并二氮唑等多种芳杂环发生取代反应,具有区域选择性地引入带有酯、酮、氰等基团的烷基侧链.这些自由基烷基化方法的发展丰富了芳杂环的修饰手段,助力了相应化合物生物、药物活性的进一步研究.Aromatic heterocycles are crucial drug scaffolds,and the radical alkylation is an efficient method for their modification.Intermolecular radical alkylation of aromatic heterocycles using xanthates since 2003 has been reviewed.Xanthates can be irradiated by peroxides,such as lauroyl peroxide,at elevated temperature;they are able to be triggered by trialkylborane/oxygen system and visible light in the presence of photosensitizers.The resulting alkyl radicals react with heterocycles,including pyrrole,indole and benzodiazole,introducing regioselectively alkyl side chains with various functional group including ester,ketone and cyano groups.The development of these radical alkylation enriches the modification method of aromatic heterocycles,which may benefit the further study of the biological and pharmaceutical activity of these molecules.

关 键 词：芳杂环 自由基反应 烷基化 黄原酸酯 区域选择性 

分 类 号：TQ251.3[化学工程—有机化工]