咪唑促进一锅法高效合成多取代2-喹啉酮类化合物  

Efficient one pot synthesis of multi-substituted 2-quinolinone compounds promoted by imidazole

作　　者：刘怡阳 樊荣荣 白育斌 黄亮珠 LIU Yiyang;FAN Rongrong;BAI Yubin;HUANG Liangzhu(School of Chemistry and Chemical Engineering,Yan’an University;Shaanxi Key Laboratory of Chemical Reaction Engineering;Institute for Triazine Compounds&Hierarchical Porous Materials,Yan’an 716000,China)

机构地区：[1]延安大学化学与化工学院 [2]陕西省化学反应工程重点实验室 [3]三嗪化合物与多级孔材料研究所,陕西延安716000

出　　处：《延安大学学报（自然科学版）》2023年第3期7-12,共6页Journal of Yan'an University：Natural Science Edition

基　　金：陕西省科技厅自然科学基金项目(2021JQ-716);延安大学博士科研启动基金项目(YDBK2019-02)。

摘　　要：2-喹啉硐类化合物是主要的有机合成中间体。报道了咪唑促进的2-胺基二苯甲酮与丙二酸酯单酰氯在温和条件下的高效缩合、加成、环化反应,能以70%~99%的分离产率合成不同取代2-喹啉酮类含氮杂环化合物,具有很好的底物适用性。该反应无需惰性气体保护,可在空气中反应,操作简单,易于放大生产。反应机理研究表明,使用的咪唑既可以作为酰胺化的缚酸剂,过量的咪唑同时可以催化分子内的羟醛缩合反应,从而实现一锅法高效合成多取代2-喹啉酮含氮杂环化合物,为含有2-喹啉酮骨架的天然产物或药物的合成提供了有效的合成方法。This paper rpresents the highly efficient condensation,addition and cyclization reaction in one-pot by using 2-aminobenzophenone and malonate monoacyl chloride promoted by imidazole under mild conditions,which can synthesize different substituted 2-quinolinone nitrogen-containing Heterocyclic compounds with 70~99%isolated yield,and has good substrate applicability.This reaction does not require inert gas protection and can react under air,making it easy to operate and scale up production.The study on the reaction mechanism shows that the imidazole can not only be used as an acid binding agent for amidation,but also can catalyze the intramolecular Aldol condensation reaction at the same time,so as to achieve a one pot efficient synthesis of polysubstituted 2-quinolinone nitrogen-containing heterocyclic compounds,providing an effective synthetic method for the synthesis of natural product or drugs containing 2-quinolinone skeleton.

关 键 词：碱催化 咪唑 分子内加成环化反应 2-喹啉酮类化合物 

分 类 号：O626.4[理学—有机化学]