CuI催化无溶剂一锅法合成苯二氮酮类化合物  

One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI

作　　者：张青扬[1] 汪小涧[1] 肖琼[1] 尹大力[1] 

机构地区：[1]北京协和医学院&中国医学科学院药物研究所,天然药物活性物质与功能国家重点实验室,活性物质发现与适药化研究北京重点实验室,北京100050

出　　处：《有机化学》2017年第4期954-958,共5页Chinese Journal of Organic Chemistry

摘　　要：含苯二氮?酮母核的化合物是一类具有重要生理活性的有机杂环化合物.以邻溴代苯甲酸乙酯和邻二胺类化合物为原料,在无溶剂状态下,通过Cu I催化偶联并进一步内酰胺化关环,一锅法合成了目标化合物.该方法绿色环保、反应条件温和、操作简便、一步反应且收率较高.通过最优的反应条件下,研究了一系列不同芳香环取代基对反应的影响,并验证了此方法能用于不同取代芳香二氮?酮类化合物的合成.在此基础上,将此合成方法应用于一些含有苯二氮?酮结构的生物活性化合物的合成,并取得满意的结果.Benzodiazepinones are the important class of organic heterocyclic compounds with physiological activities. Here- in, one pot procedure for the synthesis of benzodiazepinones has been developed under solvent-free condition. The substituted ethyl 2-bromobenzoates were cross-coupled with adjacent diamine compounds using CuI as a catalyst to give the intermedi- ates, which spontaneously underwent an intramolecular N-acylation producing corresponding benzodiazepinones. This method has the advantages of enviroment frendly, mild reaction conditions, simple one pot operation and high yields. Under the opti- mized conditions, the effect of various substituted group on the reaction was investigated and the tolerance of this system was evaluated. This protocol could tolerate a variety of functional groups, and provide efficient access to a wide variety of substi- tuted benzodiazepinones in good yields, including biological active molecules.

关 键 词：无溶剂 一锅法 碘化亚铜 苯二氮■酮 催化偶联 

分 类 号：O621.251[理学—有机化学]