Lewis酸催化三组分合成喹啉-2,4-二羧酸酯类化合物  

Synthesis of Quinoline-2,4-dicarboxylate Compounds Based on Three-Component Coupling Catalyzed by Lewis Acid

作　　者：程正载 王云 谢聪[2] 唐然 王涵鼎 丁玲 刘锋波 颜晓潮 朱三勇 Mario Gauthier CHENG Zhengzai;WANG Yun;XIE Cong;TANG Ran;WANG Handing;DING Ning;LIU Fengbo;YAN Xiaochao;ZHU Sanyong;Mario Gauthier(Research Institute of Fine Organic Chemicals & Organic Materials at School of Chemistry and Chemical Engineering,Wuhan University of Science and Technology,Wuhan 430081,China;Hubei Collaboration Innovative Center for Non-Power Nuclear Technology,Hubei University of Science and Technology,Xianning 437100,China;Chemistry Department,University of Florida,FLGNV 32611,American)

机构地区：[1]武汉科技大学化学与化工学院,精细有机化工与有机材料研究所,湖北武汉430081 [2]湖北科技学院湖北省非动力核技术协同创新中心,湖北咸宁437100 [3]弗罗里达大学化学系,盖恩斯威尔32611

出　　处：《湖南大学学报(自然科学版)》2018年第6期133-138,共6页Journal of Hunan University:Natural Sciences

基　　金：湖北省自然科学基金资助项目(2017CFB680),湖北省教育厅中青年人才项目(Q20162806);煤转化与新型炭材料湖北省重点实验室开放基金资助项目(WKDM201509);国家大学生科学基金资助项目(201510488004).

摘　　要：采用价廉易得的无水三氯化铝、三氯化铁、氯化铜等Lewis酸催化取代芳胺、乙醛酸乙酯和丙酮酸甲酯三组分一步反应,高效合成了4个喹啉-2,4-二羧酸酯类化合物.产物通过柱层析分离纯化,并采用FT-IR、~1H NMR、^(13)C NMR和元素分析等手段进行了结构表征.探讨了反应机理和取代芳胺的分子结构对反应的影响规律,为该类新颖化合物的分子设计与合成方法提供参考.该方法具有原料廉价易得、反应条件温和、原子经济性高、产率高等优点.An efficient method for synthesizing quinoline-2,4-dicarboxylate compounds was developed via a one-pot reaction of catalyzed lewis acid such as cheap and easily obtained AlCl 3, CuCl 2 and FeCl 3 instead of aromatic amines, ethyl glyoxylate and methyl pyruvate. The major products were separated and purified by thin-layer chromatography, and their structures were characterized by FT-IR, 1H NMR, 13 C NMR and elemental analysis. The reaction mechanism and the influence of substituents attached to aromatic amine for the reaction were discussed, which will provide a useful reference for molecular design and synthesis of this kind of novel compounds in the future. This method has some advantages such as cheap materials, mild reaction conditions, high atom economy and high yield.

关 键 词：芳胺 乙醛酸乙酯 丙酮酸甲酯 LEWIS酸 喹啉衍生物 

分 类 号：TQ031.2[化学工程]