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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Visible Light Mediated, Catalyst Free, One-Pot Convenient Synthesis of Dihydropyridines

Author(s): Jia-Qi Di, Meng-Nan Chen, Ai-Dong Zhao* and Zhan-Hui Zhang*

Volume 19, Issue 4, 2022

Published on: 25 January, 2021

Page: [276 - 282] Pages: 7

DOI: 10.2174/1570178618666210125162342

Price: $65

Abstract

A simple, efficient and green protocol has been developed for the synthesis of polysubstituted dihydropyridines via one-pot, four-component reaction of aldehydes, arylamines, dialkyl acetylenedicarboxylate, and malononitrile. The reaction was proceeded at room temperature in the absence of catalyst in aqueous ethyl lactate under visible light irradiation. The main advantages of the present approach are mild reaction conditions, high yield, no column chromatography, clean reaction profile, environmentally friendly and sustainability from the economic point of view.

Keywords: Catalyst-free, dihydropyridine, green chemistry, multi-component reaction, visible light.

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[1]
Chen, M.N.; Mo, L.P.; Cui, Z.S.; Zhang, Z.H. Curr. Opin. Green. Sustain. Chem., 2019, 15, 27-37.
[http://dx.doi.org/10.1016/j.cogsc.2018.08.009]
[2]
Wang, Y.D.; Tao, L.L.; Chen, J.; He, W.M.; Deng, H.M.; Shao, M.; Zhang, H.; Cao, W.G. Asian J. Org. Chem., 2019, 8, 710-715.
[http://dx.doi.org/10.1002/ajoc.201900010]
[3]
Zhang, M.; Liu, Y.H.; Shang, Z.R.; Hu, H.C.; Zhang, Z.H. Catal. Commun., 2017, 88, 39-44.
[http://dx.doi.org/10.1016/j.catcom.2016.09.028]
[4]
Azimi, R.; Lasemi, Z.; Hashkavayi, A.B. Lett. Org. Chem., 2020, 17, 268-280.
[http://dx.doi.org/10.2174/1570178616666190618113635]
[5]
Mohammadzadeh, I.; Asadipour, A.; Pardakhty, A.; Abaszadeh, M. Lett. Org. Chem., 2020, 17, 240-245.
[http://dx.doi.org/10.2174/1570178616666190620124947]
[6]
Nadaf, A.N.; Shivashankar, K. Lett. Org. Chem., 2019, 16, 676-682.
[http://dx.doi.org/10.2174/1570178615666181107095151]
[7]
Zhang, M.; Sun, W.; Lv, H.; Zhang, Z.H. Curr. Opin. Green. Sustain. Chem., 2021, 27, 100390.
[http://dx.doi.org/10.1016/j.cogsc.2020.100390]
[8]
Fu, W.; Han, X.; Zhu, M.; Xu, C.; Wang, Z.; Ji, B.; Hao, X.Q.; Song, M.P. Chem. Commun., 2016, 52(91), 13413-13416.
[http://dx.doi.org/10.1039/C6CC07771D] [PMID: 27790647]
[9]
Zhu, M.; Han, X.; Fu, W.; Wang, Z.; Ji, B.; Hao, X.Q.; Song, M.P.; Xu, C. J. Org. Chem., 2016, 81(16), 7282-7287.
[http://dx.doi.org/10.1021/acs.joc.6b00950] [PMID: 27328667]
[10]
Zhu, M.; Li, R.X.; You, Q.Q.; Fu, W.J.; Guo, W.S. Asian J. Org. Chem., 2019, 8, 2002-2005.
[http://dx.doi.org/10.1002/ajoc.201900499]
[11]
Xie, L.Y.; Liu, Y.S.; Ding, H.R.; Gong, S.F.; Tan, J.X.; He, J.Y.; Cao, Z.; He, W.M. Chin. J. Catal., 2020, 41, 1168-1173.
[http://dx.doi.org/10.1016/S1872-2067(19)63526-6]
[12]
Chen, D.; Liu, J.C.; Zhang, X.Y.; Jiang, H.Z.; Li, J.H. Chin. J. Org. Chem., 2019, 39, 3353-3362.
[http://dx.doi.org/10.6023/cjoc201907014]
[13]
Gawande, M.B.; Bonifácio, V.D.B.; Luque, R.; Branco, P.S.; Varma, R.S. Chem. Soc. Rev., 2013, 42(12), 5522-5551.
[http://dx.doi.org/10.1039/c3cs60025d] [PMID: 23529409]
[14]
Zhang, M.; Chen, M-N.; Li, J-M.; Liu, N.; Zhang, Z.H. ACS Comb. Sci., 2019, 21(10), 685-691.
[http://dx.doi.org/10.1021/acscombsci.9b00124] [PMID: 31433619]
[15]
Zhang, M.; Chen, M.N.; Zhang, Z.H. Adv. Synth. Catal., 2019, 361, 5182-5190.
[http://dx.doi.org/10.1002/adsc.201900994]
[16]
Yadav, S.; Srivastava, M.; Rai, P.; Singh, J.; Tiwari, K.P.; Singh, J. New J. Chem., 2015, 39, 4556-4561.
[http://dx.doi.org/10.1039/C5NJ00002E]
[17]
Mohammadi, H.; Shaterian, H.R. ChemistrySelect, 2018, 3, 11059-11064.
[http://dx.doi.org/10.1002/slct.201802083]
[18]
Shivhare, K.N.; Jaiswal, M.K.; Srivastava, A.; Tiwari, S.K.; Siddiqui, I.R. New J. Chem., 2018, 42, 16591-16601.
[http://dx.doi.org/10.1039/C8NJ03339K]
[19]
Chen, M.N.; Di, J.Q.; Li, J.M.; Mo, L.P.; Zhang, Z.H. Tetrahedron, 2020, 76131059.
[http://dx.doi.org/10.1016/j.tet.2020.131059]
[20]
Safak, C.; Simsek, R. Mini Rev. Med. Chem., 2006, 6(7), 747-755.
[http://dx.doi.org/10.2174/138955706777698606] [PMID: 16842124]
[21]
Khedkar, S.A.; Auti, P.B. Mini Rev. Med. Chem., 2014, 14(3), 282-290.
[http://dx.doi.org/10.2174/1389557513666131119204126] [PMID: 24251802]
[22]
Viradiya, D.; Mirza, S.; Shaikh, F.; Kakadiya, R.; Rathod, A.; Jain, N.; Rawal, R.; Shah, A. Anticancer. Agents Med. Chem., 2017, 17(7), 1003-1013.
[http://dx.doi.org/10.2174/1871520616666161206143251] [PMID: 27924733]
[23]
Mahmoodi, N.O.; Ramzanpour, S.; Pirbasti, F.G. Arch. Pharm., 2015, 348, 275-282.
[http://dx.doi.org/10.1002/ardp.201400414]
[24]
Malek, R.; Maj, M.; Wnorowski, A.; Jóźwiak, K.; Martin, H.; Iriepa, I.; Moraleda, I.; Chabchoub, F.; Marco-Contelles, J.; Ismaili, L. Bioorg. Chem., 2019, 91, 103205.
[http://dx.doi.org/10.1016/j.bioorg.2019.103205] [PMID: 31446330]
[25]
Lentz, F.; Reiling, N.; Spengler, G.; Kincses, A.; Csonka, A.; Molnar, J.; Hilgeroth, A. Molecules, 2019, 24, 2873.
[http://dx.doi.org/10.3390/molecules24162873]
[26]
Lu, Z.; Yang, Y.Q. Synthesis, 2019, 51, 508-515.
[http://dx.doi.org/10.1055/s-0037-1610629]
[27]
Wan, J.P.; Liu, Y.Y. RSC Advances, 2012, 2, 9763-9777.
[http://dx.doi.org/10.1039/c2ra21406g]
[28]
Ramesh, R.; Arivazhagan, M.; Malecki, J.G.; Lalitha, A. Synlett, 2018, 29, 1897-1901.
[http://dx.doi.org/10.1055/s-0037-1609579]
[29]
Neamani, S.; Moradi, L. ChemistrySelect, 2020, 5, 7439-7446.
[http://dx.doi.org/10.1002/slct.202002146]
[30]
Baghery, S.; Zolfigol, M.A. J. Mol. Liq., 2017, 232, 174-181.
[http://dx.doi.org/10.1016/j.molliq.2017.02.073]
[31]
Ghasemzadeh, M.A.; Abdollahi-Basir, M.H. Acta Chim. Slov., 2016, 63(3), 627-637.
[http://dx.doi.org/10.17344/acsi.2016.2386] [PMID: 27640390]
[32]
Khan, M.M. ChemistrySelect, 2018, 3, 6830-6835.
[http://dx.doi.org/10.1002/slct.201800709]
[33]
Pal, S.; Khan, M.N.; Choudhury, L.H. J. Heterocycl. Chem., 2014, 51, E156-E162.
[http://dx.doi.org/10.1002/jhet.1914]
[34]
Chen, H.S.; Guo, R.Y. Monatsh. Chem., 2015, 146, 1355-1362.
[http://dx.doi.org/10.1007/s00706-015-1416-9]
[35]
Sun, J.; Xia, E.Y.; Wu, Q.; Yan, C.G. Org. Lett., 2010, 12(16), 3678-3681.
[http://dx.doi.org/10.1021/ol101475b] [PMID: 20704414]
[36]
Han, Y.; Zhang, M.; Zhang, Y.Q.; Zhang, Z.H. Green Chem., 2018, 20, 4891-4900.
[http://dx.doi.org/10.1039/C8GC02611D]
[37]
Pal, S.; Choudhury, L.H.; Parvin, T. Synth. Commun., 2013, 43, 986-992.
[http://dx.doi.org/10.1080/00397911.2011.618283]
[38]
Mashaly, M.M.; El-Gogary, S.R.; Kosbar, T.R. J. Heterocycl. Chem., 2014, 51(4), 1078-1085.
[http://dx.doi.org/10.1002/jhet.1609]

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