Citation: 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. doi: 10.6023/cjoc201909006 shu

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

Corresponding author: Li Ningbo, ningboli@sxmu.edu.cn
Received Date: 3 September 2019
Revised Date: 30 October 2019
Available Online: 11 December 2019
Fund Project: the National Natural Science Foundation of China 21802093the Scientific and Technologial Innovation Programs of Higher Education Institutions in Shanxi 2019L0408Project 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)the Shanxi Province Science Foundation for Youths 201701D221035

Figures(2)

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.
- β-naphthol formaldehyde Schiff base,
- zirconium perfluorooctanesulfonate,
- Hantzsch reaction,
- 1, 4-dihydro-pyridine,
- 4-aryl polyhydroquinoline
1. [1]
  Chen, G. H.; Wang, L.; Yao, X. M.; Zhang, M. L.; Wu, F. H. Chin. J. Org. Chem. 2010, 30, 997(in Chinese).
2. [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. doi: 10.1021/jm00001a017
3. [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. doi: 10.1021/jm031109v
4. [4]
  Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F. Drugs Future 1992, 17, 465. doi: 10.1358/dof.1992.017.06.175816
5. [5]
  Plowright, A. T.; Schaus, S. E.; Myers, A. G. Chem. Biol. 2002, 9, 607. doi: 10.1016/S1074-5521(02)00137-0
6. [6]
  Maheswara, M.; Siddaiah, V.; Rao, Y. K.; Tzeng, Y. M.; Sridhar, C. J. Mol. Catal. A:Chem. 2006, 260, 179. doi: 10.1016/j.molcata.2006.07.024
7. [7]
  Debache, A.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Synlett 2008, 509. doi: 10.1055/s-2008-1032093
8. [8]
  Kumar, A.; Maurya, R. A. Synlett 2008, 883. doi: 10.1055/s-2008-1042908
9. [9]
  Arslan, M.; Faydali, C.; Zengin, M.; Kucukislamoglu, M.; Demirhan, H. Turk. J. Chem. 2009, 33, 769. doi: 10.3906/kim-0812-5
10. [10]
  Datta, B.; Pasha, M. A. Chin. J. Catal. 2011, 32, 1180. doi: 10.1016/S1872-2067(10)60252-5
11. [11]
  Sharma, M.; Agarwal N.; Rawat, D. S. J. Heterocycl. Chem. 2008, 45, 737. doi: 10.1002/jhet.5570450316
12. [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. doi: 10.1016/S1872-2067(12)60678-0
13. [13]
  Sharma, S. D.; Hazarika, P.; Konwar, D. A. Catal. Commun. 2008, 9, 709. doi: 10.1016/j.catcom.2007.08.008
14. [14]
  Wang, L. M.; Sheng, J.; Zhang, L.; Han, J. W.; Fan, Z. Y.; Tian, H.; Qian, C. T. Tetrahedron 2005, 61, 1539. doi: 10.1016/j.tet.2004.11.079
15. [15]
  Hong, M.; Cai, C.; Yi, W. B. J. Fluorine Chem. 2010, 131, 111. doi: 10.1016/j.jfluchem.2009.10.009
16. [16]
  Shaabani, A.; Rezayan, A. H.; Rahmati, A.; Sharifi, M. Monatsh. Chem. 2006, 137, 77. doi: 10.1007/s00706-005-0405-9
17. [17]
  Reddy, B. P.; Rajesh, K.; Vijayakumar, V. J. J. Chin. Chem. Soc. (Peking) 2011, 58, 384. doi: 10.1002/jccs.201190041
18. [18]
  Salehi, H.; Guo, Q. X. Synth. Commun. 2004, 34, 4349. doi: 10.1081/SCC-200039409
19. [19]
  Chari, M. A.; Syamasundar, K. Catal. Commun. 2005, 6, 624. doi: 10.1016/j.catcom.2005.03.010
20. [20]
  Bridgwood, K. L.; Veitch, G. E.; Ley, S. V. Org. Lett. 2008, 10, 3627. doi: 10.1021/ol801399w
21. [21]
  Debache, A.; Ghalem, W.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2009, 50, 5248. doi: 10.1016/j.tetlet.2009.07.018
22. [22]
  Saha, M.; Pal, A. K. Tetrahedron Lett. 2011, 52, 4872. doi: 10.1016/j.tetlet.2011.07.031
23. [23]
  Rostamnia, S.; Morsalib, A. RSC Adv. 2014, 4, 10514. doi: 10.1039/c3ra46709k
24. [24]
  Rostamnia, S.; Alamgholiloo, H.; Jafari M. Appl. Organomet. Chem. 2018, 32, 4370. doi: 10.1002/aoc.4370
25. [25]
  Tan, J.; Liu, X.; Yao, N.; Hu, Y. L.; Li, X. H. ChemistrySelect 2019, 4, 2475. doi: 10.1002/slct.201803739
26. [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).
27. [27]
  Górski, Ł.; Matusevich, A.; Parzuchowski, P.; Łuciuk, I.; Malinowska, E. Anal. Chim. Acta 2010, 665, 39. doi: 10.1016/j.aca.2010.03.021
28. [28]
  Jafarpour, M.; Rezaeifard, A.; Gorzin, G. Inorg. Chem. Commun. 2011, 14, 1732. doi: 10.1016/j.inoche.2011.07.017
29. [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. doi: 10.1002/cctc.201800590
30. [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. [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).
32. [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. doi: 10.1016/j.inoche.2018.10.010
33. [33]
  Li, N. B.; Qiu, R. H.; Zhang, X. H.; Chen, Y.; Yin, S. F.; Xu, X. H. Tetrahedron 2015, 71, 4275. doi: 10.1016/j.tet.2015.05.013
34. [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. doi: 10.1039/C4DT00549J
35. [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. doi: 10.1016/j.catcom.2013.10.013
36. [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. doi: 10.1002/adsc.201300439
37. [37]
  Lei, M.; Lei, M.; Hu, L. H. Synth. Commun. 2011, 41, 1969. doi: 10.1080/00397911.2010.494814
38. [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).
39. [39]
  Zhang, Y. H.; Zhang, Z. Q.; Wu, Q. Acta Pharm. Sin. 1991, 26, 375(in Chinese).
40. [40]
  Li, B. L.; Zhong, A. G. Ying, A. G. J. Heterocycl. Chem. 2015, 52, 445. doi: 10.1002/jhet.2070
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