新型席夫碱锆路易斯酸催化1,4-二氢吡啶和多氢喹啉高效合成  

Efficient Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines Catalyzed by Novel Schiff Base Zirconium Lewis Acid

作　　者：王静[1] 靳朝晖 马榕 郝英健 王一钧 李宁波 许新华[3] Wang Jing;Jin Zhaohui;Ma Rong;Hao Yinjian;Wang Yijun;Li Ningbo;XuXinhua(Department of Preventive Medicine,School of Public Health,Shanxi Medical University,Taiyuan 030001;Basic Medical College,Shanxi Medical University,Taiyuan 030001;College of Chemistry and Chemical Engineering,Hunan University,Changsha 410082)

机构地区：[1]山西医科大学公共卫生学院预防医学系,太原030001 [2]山西医科大学基础医学院,太原030001 [3]湖南大学化学化工学院,长沙410082

出　　处：《有机化学》2020年第4期969-977,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21802093);山西省青年科学基金(No.201701D221035);山西省高等学校科技创新(No.2019L0408)资助项目.

摘　　要：合成了一种新型对空气稳定的β-萘酚醛席夫碱锆全氟辛基磺酸盐路易斯酸催化剂.该催化剂由β-萘酚醛席夫碱锆二氯化物与全氟辛基磺酸银在室温下避光反应制得.催化活性实验表明,在80℃和无溶剂条件下,该催化剂(5 mol%)能够高效催化醛、β-酮酯和醋酸铵的Hantzsch反应制备1,4-二氢吡啶化合物;也可以高效催化芳香醛、环状β-二酮、β-酮酯和醋酸铵的反应制备4-芳基多氢喹啉化合物.催化剂在重复使用五次之后,产率没有明显降低,为1,4-二氢吡啶和4-芳基多氢喹啉化合物的制备提供了一条简单有效的途径.A novel air-stableβ-naphthol formaldehyde Schiff base zirconium perfluorooctanesulfonate Lewis acid catalyst was successfully synthesized by the reaction ofβ-naphthol formaldehyde Schiff base zirconium dichlorides with silver perfluorooctanesulfonate in the absence of light at room temperature.The results of catalytic assessment showed that this complex(5 mol%)could effectively catalyze the Hantzsch reaction of aldehydes,β-keto ester and ammonium acetate to obtain 1,4-dihydropyridine compounds at 80℃under solvent-free conditions in good to excellent yields.Meanwhile,it could also effectively catalyze the reaction of aromatic aldehydes,cyclicβ-diketone,β-keto ester and ammonium acetate to obtain 4-aryl polyhydroquinoline compounds.This catalyst could be reused 5 times,and the yields had no significant decrease.This procedure provides a simple and efficient way for the synthesis of 1,4-dihydropyridine and polyhydroquinoline compounds.

关 键 词：β-萘酚醛席夫碱 锆全氟辛基磺酸配合物 Hantzsch反应 1 4-二氢吡啶 4-芳基多氢喹啉 

分 类 号：O643.36[理学—物理化学] O626.32[理学—化学]