CuI催化的A^(3)-偶联反应合成邻羟基苯基丙炔胺类化合物的研究  

CuI-catalyzed A^(3)-Coupling Reactions for the Synthesis of o-Hydroxyphenyl Propargylamines

作　　者：樊陈莉[1,2] 谢吉娜 惠文杰 陈浩宇 何心伟[2] FAN Chen-li;XIE Ji-na;HUIWen-jie;CHEN Hao-yu;HE Xin-wei(Department of Material Engineering,Wuhu Institute of Technology,Wuhu 241003,China;College of Chemistry and Materials Science,Anhui Normal University,Wuhu 241002,China)

机构地区：[1]芜湖职业技术学院材料工程学院,安徽芜湖241003 [2]安徽师范大学化学与材料科学学院,安徽芜湖241002

出　　处：《安徽师范大学学报（自然科学版）》2023年第2期138-145,共8页Journal of Anhui Normal University(Natural Science)

基　　金：安徽省精品在线开放课程项目(2021jpkc195);安徽师范大学大学生创新创业训练计划项目:(202110370021,202210370052,X202210370023);安徽省教学创新团队(2022cxtd169).

摘　　要：丙炔胺类化合物因其具有多个反应位点而在有机合成中具有广泛的应用。本文发展了一种CuI催化的水杨醛、四氢吡咯和末端炔的A^(3)-偶联反应合成邻羟基苯基丙炔胺衍生物的方法。水杨醛和芳基乙炔中无论是吸电子基团还是供电子基团均能较好的适用于该反应,且水杨醛中含有多个取代基时也能得到相应的目标产物,并利用^(1)H,^(13)C NMR和HRMS等手段对目标化合物的结构进行了表征。该合成方法具有操作简单、合成效率高和取代基容忍性好等优点,为邻羟基苯基丙炔胺类化合物的合成提供了一种新的合成思路。Propargylamine compounds have been widely used in organic synthesis because of their multiple reaction sites,and thus have attracted extensive attention.In this paper,a CuI-catalyzed A^(3)-coupling reactions of salicyladehydes,pyrrolidine and terminal alkynes for the synthesis of propargylamines has been developed.Salicyladehydes and aromatic alkynes bearing with electron-withdrawing or electron-donating groups were well tolerated.In particular,disubtituted salicyladehydes were investigated to showcase the prospective utility of this protocol.Moreover,all products were characterized by ^(1)H,^(13)C NMR and HRMS.The results showed that the method has the advantages of wide scope of substrates,good tolerance of substituents,and without separation of intermediates by using multi-component one-pot reaction,achieving step economy and application in organic synthesis.

关 键 词：A^(3)-偶联反应 丙炔胺 水杨醛 苯乙炔 

分 类 号：O626[理学—有机化学]