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

doi:10.6023/cjoc201909006

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 969-977.DOI: 10.6023/cjoc201909006 Previous Articles Next Articles

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

王静^a, 靳朝晖^b, 马榕^b, 郝英健^b, 王一钧^b, 李宁波^b, 许新华^c

a 山西医科大学公共卫生学院预防医学系太原 030001;
b 山西医科大学基础医学院太原 030001;
c 湖南大学化学化工学院长沙 410082

收稿日期:2019-09-03 修回日期:2019-10-30 发布日期:2020-05-06
通讯作者: 李宁波 E-mail:ningboli@sxmu.edu.cn
基金资助:
国家自然科学基金（No.21802093）、山西省青年科学基金（No.201701D221035）和山西省高等学校科技创新（No.2019L0408）资助项目.

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

Wang Jing^a, Jin Zhaohui^b, Ma Rong^b, Hao Yinjian^b, Wang Yijun^b, Li Ningbo^b, Xu Xinhua^c

a Department of Preventive Medicine, School of Public Health, Shanxi Medical University, Taiyuan 030001;
b Basic Medical College, Shanxi Medical University, Taiyuan 030001;
c College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2019-09-03 Revised:2019-10-30 Published:2020-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21802093), the Shanxi Province Science Foundation for Youths (No. 201701D221035) and the Scientific and Technologial Innovation Programs of Higher Education Institutions in Shanxi (No. 2019L0408).

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Abstract

A novel air-stable β-naphthol formaldehyde Schiff base zirconium perfluorooctanesulfonate Lewis acid catalyst was successfully synthesized by the reaction of β-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, cyclic β-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.

Key words: β-naphthol formaldehyde Schiff base, zirconium perfluorooctanesulfonate, Hantzsch reaction, 1,4-dihydro-pyridine, 4-aryl polyhydroquinoline

Cite this article

Wang Jing, Jin Zhaohui, Ma Rong, Hao Yinjian, Wang Yijun, Li Ningbo, Xu Xinhua. Efficient Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines Catalyzed by Novel Schiff Base Zirconium Lewis Acid[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 969-977.

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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

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