廉价铜催化喹啉类化合物的高效构建  

Efficient synthesis of quinolones enabled by cheap copper catalysis

作　　者：李怡霏 张菁 胡小强 LI Yifei;ZHANG Jing;HU Xiaoqiang(College of Chemistry and Materials Science,South-Central Minzu University,Wuhan 430074,China)

机构地区：[1]中南民族大学化学与材料科学学院,武汉430074

出　　处：《中南民族大学学报（自然科学版）》2023年第3期300-305,共6页Journal of South-Central University for Nationalities：Natural Science Edition

基　　金：国家自然科学基金资助项目(21901258,22271314)。

摘　　要：报道了一例CuSO_(4)‧5H_(2)O催化胺茴内酐与1,3-环己二酮的开环、缩合环化串联反应,实现了喹啉类衍生物的高效合成.该法具有铜催化剂便宜易得、操作简单和收率良好等优点,为喹啉类化合物的高效合成提供了一个新的方法.进一步结果表明:1,3-环戊二酮和丁炔酸二甲酯也适用于该体系,有效拓展了底物范围,以中等的收率获得多取代喹啉类化合物,此外还提出了一种铜催化胺茴内酐开环、缩合环化串联反应机理.An efficient CuSO_(4)‧5H_(2)O-catalyzed ring-opening,condensation and annulation cascade reaction of anthranils with 1,3-cyclohexanedione was developed for the rapid synthesis of quinoline derivatives.This method features cheap and easily available copper-catalyst,simple operation and high reaction efficiency,which provides a new approach for the efficient synthesis of quinolines.Further results showed that 1,3-cyclopentanedione and dimethyl acetylenedicarboxylate were also suitable for this system,thus effectively expanded the range of substrates to obtain polysubstituted quinolines in moderate yields.In addition,a possible Cu-catalyzed ring-opening,condensation and annulation pathway of anthranylides was proposed to explain the cascade reaction mechanism.

关 键 词：铜催化 胺茴内酐 1 3-环己二酮 喹啉 环化反应 

分 类 号：O626.42[理学—有机化学]