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

doi:10.6023/cjoc201909006

有机化学 ›› 2020, Vol. 40 ›› Issue (4): 969-977.DOI: 10.6023/cjoc201909006 上一篇下一篇

研究论文

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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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

引用此文

王静, 靳朝晖, 马榕, 郝英健, 王一钧, 李宁波, 许新华. 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[J]. 有机化学, 2020, 40(4): 969-977.

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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参考文献

[1] Chen, G. H.; Wang, L.; Yao, X. M.; Zhang, M. L.; Wu, F. H. Chin. J. Org. Chem. 2010, 30, 997(in Chinese). (陈国华, 王丽, 姚秀梅, 张明亮, 吴斐华, 有机化学, 2010, 30, 997.)
[2] Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Di-marco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; Macarthy, J. P.; Zhang, R.; Mereland, S. J. Med. Chem. 1995, 38, 119.
[3] Visentin, S.; Rolando, B.; Distlio, A.; Frutterro, R.; Novara, M.; Carbone, E.; Roussel, C.; Vanthuyne, N.; Gasco, A. J. Med. Chem. 2004, 47, 2688.
[4] Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F. Drugs Future 1992, 17, 465.
[5] Plowright, A. T.; Schaus, S. E.; Myers, A. G. Chem. Biol. 2002, 9, 607.
[6] Maheswara, M.; Siddaiah, V.; Rao, Y. K.; Tzeng, Y. M.; Sridhar, C. J. Mol. Catal. A:Chem. 2006, 260, 179.
[7] Debache, A.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Synlett 2008, 509.
[8] Kumar, A.; Maurya, R. A. Synlett 2008, 883.
[9] Arslan, M.; Faydali, C.; Zengin, M.; Kucukislamoglu, M.; Demirhan, H. Turk. J. Chem. 2009, 33, 769.
[10] Datta, B.; Pasha, M. A. Chin. J. Catal. 2011, 32, 1180.
[11] Sharma, M.; Agarwal N.; Rawat, D. S. J. Heterocycl. Chem. 2008, 45, 737.
[12] Khazaei, A.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Afsar, J.; Zare, A.; Khakyzadeh, V.; Beyzavi, M. H. Chin. J. Catal. 2013, 34, 1936.
[13] Sharma, S. D.; Hazarika, P.; Konwar, D. A. Catal. Commun. 2008, 9, 709.
[14] Wang, L. M.; Sheng, J.; Zhang, L.; Han, J. W.; Fan, Z. Y.; Tian, H.; Qian, C. T. Tetrahedron 2005, 61, 1539.
[15] Hong, M.; Cai, C.; Yi, W. B. J. Fluorine Chem. 2010, 131, 111.
[16] Shaabani, A.; Rezayan, A. H.; Rahmati, A.; Sharifi, M. Monatsh. Chem. 2006, 137, 77.
[17] Reddy, B. P.; Rajesh, K.; Vijayakumar, V. J. J. Chin. Chem. Soc. (Peking) 2011, 58, 384.
[18] Salehi, H.; Guo, Q. X. Synth. Commun. 2004, 34, 4349.
[19] Chari, M. A.; Syamasundar, K. Catal. Commun. 2005, 6, 624.
[20] Bridgwood, K. L.; Veitch, G. E.; Ley, S. V. Org. Lett. 2008, 10, 3627.
[21] Debache, A.; Ghalem, W.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2009, 50, 5248.
[22] Saha, M.; Pal, A. K. Tetrahedron Lett. 2011, 52, 4872.
[23] Rostamnia, S.; Morsalib, A. RSC Adv. 2014, 4, 10514.
[24] Rostamnia, S.; Alamgholiloo, H.; Jafari M. Appl. Organomet. Chem. 2018, 32, 4370.
[25] Tan, J.; Liu, X.; Yao, N.; Hu, Y. L.; Li, X. H. ChemistrySelect 2019, 4, 2475.
[26] Yi, W. G.; Jia, Z. Y.; Li, N. B.; Qiu, R. H.; Chen, J. Y.; Xu, X. H. Chin. J. Org. Chem. 2012, 32, 2390(in Chinese). (易卫国, 贾振永, 李宁波, 邱仁华, 陈锦杨, 许新华, 有机化学, 2012, 32, 2390.)
[27] Górski, Ł.; Matusevich, A.; Parzuchowski, P.; Łuciuk, I.; Malinowska, E. Anal. Chim. Acta 2010, 665, 39.
[28] Jafarpour, M.; Rezaeifard, A.; Gorzin, G. Inorg. Chem. Commun. 2011, 14, 1732.
[29] Li, N. B.; Wang, L. X.; Zhang, L. T.; Zhao, W. J.; Qiao, J.; Xu, X. H.; Liang, Z. W. ChemCatChem 2018, 10, 3532.
[30] Li, N. B.; Wang, L. X.; Wang, H. J.; Qiao, J.; Zhao, W. J.; Xu, X. H.; Liang, Z. W. Tetrahedron 2018, 74, 1038.
[31] Wang, L. X.; Li, N. B.; Wang, H. J.; Liu, W.; Diao, H. P.; Xu, X. H. Chin. J. Org. Chem. 2019, 39, 1802(in Chinese). (王灵晓, 李宁波, 王浩江, 刘文, 刁海鹏, 许新华, 有机化学, 2019, 39, 1802.)
[32] Li, N. B.; Yao, J.; Wang, L. X.; Wei, J. C.; Liu, W.; Liu, W. Q.; Xu, X. H.; Liang, Z. W. Inorg. Chem. Commun. 2018, 98, 99.
[33] Li, N. B.; Qiu, R. H.; Zhang, X. H.; Chen, Y.; Yin, S. F.; Xu, X. H. Tetrahedron 2015, 71, 4275.
[34] Li, N. B.; Wang, J. Y.; Zhang, X. H.; Qiu, R. H.; Wang, X.; Chen, J. Y.; Yin, S. F.; Xu, X. H. Dalton. Trans. 2014, 43, 11696.
[35] Li, N. B.; Wang, X.; Qiu, R. H.; Xu, X. H.; Chen, J. Y.; Zhang, X. H.; Chen, S. H.; Yin, S. F. Catal. Commun. 2014, 43, 184.
[36] Li, N. B.; Zhang, X. H.; Xu, X. H.; Chen, Y.; Chen, J. Y.; Qiu, R. H.; Wang, X.; Yin, S. F. Adv. Synth. Catal. 2013, 355, 2430.
[37] Lei, M.; Lei, M.; Hu, L. H. Synth. Commun. 2011, 41, 1969.
[38] Wei, Z. Z.; Li, J. F.; Wang, Z. Y.; Li, P. H.; Wang, Y. Q. Chin. J. Org. Chem. 2017, 37, 1835(in Chinese). (魏振中, 李江飞, 王泽云, 李品华, 王永秋, 有机化学, 2017, 37, 1835.)
[39] Zhang, Y. H.; Zhang, Z. Q.; Wu, Q. Acta Pharm. Sin. 1991, 26, 375(in Chinese). (张延红, 张志琪, 吴祺, 药学学报, 1991, 26, 375.)
[40] Li, B. L.; Zhong, A. G. Ying, A. G. J. Heterocycl. Chem. 2015, 52, 445.

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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