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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

本站小编 Free考研考试/2022-02-14

摘要/Abstract



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.
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
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


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