钯催化烯基苯胺与重氮化合物的[3+2]环化反应  

Palladium-catalyzed [3+2] cyclization of alkenyl aniline with diazo compounds

作　　者：南江 张佳雯 马养民[1,2] NAN Jiang;ZHANG Jia-wen;MA Yang-min(College of Chemistry and Chemical Engineering, Shaanxi University of Science & Technology, Xi′an 710021, China;Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science & Technology, Xi′an 710021, China)

机构地区：[1]陕西科技大学化学与化工学院,陕西西安710021 [2]陕西科技大学陕西省轻化工助剂重点实验室,陕西西安710021

出　　处：《陕西科技大学学报》2019年第4期64-68,73,共6页Journal of Shaanxi University of Science & Technology

基　　金：陕西省教育厅专项科研计划项目(18JK0110);陕西科技大学博士科研启动基金项目(2017BJ-37)

摘　　要：二氢呋喃骨架化合物作为一类重要的有机合成中间体及药物分子构筑单元,广泛应用于有机合成与药物化学等领域.在醋酸钯催化作用下,以邻氨基苯乙烯为原料,重氮羰基化合物为3原子合成片段进行偶联转化,反应能够以51%~69%的产率合成七种含有季碳中心的新型二氢呋喃衍生物,并通过核磁共振氢谱、核磁共振碳谱、高分辨质谱、熔点等分析手段对产物进行了表征.该方法简洁高效,具有良好的官能团兼容性,为二氢呋喃类杂环化合物的合成提供了一条新途径,也探索拓宽了重氮羰基化合物的[n+3]环化反应.As a kind of important organic synthesis intermediates and drug molecular building blocks,dihydrofuran skeleton compounds are widely used in organic synthesis and pharmaceutical chemistry.In this paper,under the catalysis of palladium acetate,o-aminostyrene is used as raw material,and diazocarbonyl is a 3-atom synthesis fragment for coupling conversion.The reaction can synthesize seven novel dihydrofuran derivatives containing quaternary carbon centers in 51%~69% yields,and the corresponding desired products were characterized by 1H NMR, 13 C NMR,HRMS,melting point and other analytical means.The method is simple and efficient and has good functional group compatibility,which provides a new way for the synthesis of dihydrofuran heterocyclic compounds.The [ n +3] annulation reaction diazocarbonyl compounds that can participate in cyclization as a 3-atom synthesizer have also been developed.

关 键 词：过渡金属 [3+2]环化 季碳中心 二氢呋喃衍生物 重氮化合物 

分 类 号：O626[理学—有机化学]