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Letters in Organic Chemistry

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

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Research Article

Efficient Synthesis of Novel Quinolinone Derivatives via Catalyst-free Multicomponent Reaction

Author(s): Rui Du, Liangliang Han, Zhongqiang Zhou* and Victor Borovkov*

Volume 17, Issue 5, 2020

Page: [403 - 407] Pages: 5

DOI: 10.2174/1570178616666190828092728

Price: $65

Abstract

The synthesis of 3-(aryl(piperidin-1-yl)methyl)-4-hydroxyquinolin-2(1H)-one derivatives via catalyst-free multicomponent reaction is described. The reaction of 4-hydroxyquinolin-2(1H)-one, piperidine, and 4-chlorobenzaldehyde was carried out in different solvents and under solvent-free conditions at room temperature. The best solvent in terms of the yield and reaction time was found to be dichloromethane. Most substituted benzaldehydes reacted with 4-hydroxyquinolin-2(1H)-one and piperidine to afford corresponding products in good-to-excellent yields. Aldehydes with electronwithdrawing groups were more reactive to exhibit higher reaction rates. However, 2-substituted benzaldehydes did not react with 4-hydroxyquinolin-2(1H)-one and piperidine under the reaction condition. Aldehydes bearing a hydroxyl group failed to produce the corresponding products.

Keywords: 4-hydroxyquinolin-2(1H)-one, aldehyde, piperidine, quinolinone derivatives, benzaldehydes, 2-chlorobenzaldehyde.

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[1]
Michael, J.P. Nat. Prod. Rep., 2008, 25(1), 166-187.
[http://dx.doi.org/10.1039/B612168N] [PMID: 18250901]
[2]
Arya, K.; Agarwal, M. Bioorg. Med. Chem. Lett., 2007, 17(1), 86-93.
[http://dx.doi.org/10.1016/j.bmcl.2006.09.082] [PMID: 17046250]
[3]
Oeveren, A.; Motamedi, M.; Martinborough, E.; Zhao, S.; Shen, Y.; West, S.; Chang, W.; Kallel, A.; Marschke, K.B.; Lopez, F.J.; Negro-Vilar, A.; Zhi, L. Bioorg. Med. Chem. Lett., 2007, 17(6), 1527-1531.
[http://dx.doi.org/10.1016/j.bmcl.2007.01.001] [PMID: 17267219]
[4]
Zhang, R.; Jin, S.; Wan, Y.; Lin, S.; Yan, Z. Tetrahedron Lett., 2018, 59(9), 841-847.
[http://dx.doi.org/10.1016/j.tetlet.2018.01.055]
[5]
Sener, N.; Mohammed, H.J.A.; Yerlikaya, S.; Altunoglu, Y.C.; Gür, M.; Baloglu, M.C.; Sener, I. Dyes Pigments, 2018, 157, 11-19.
[http://dx.doi.org/10.1016/j.dyepig.2018.04.040]
[6]
Ahmed, N.; Brahmbhatt, K.G.; Sabde, S.; Mitra, D.; Singh, I.P.; Bhutani, K.K. Bioorg. Med. Chem., 2010, 18(8), 2872-2879.
[http://dx.doi.org/10.1016/j.bmc.2010.03.015] [PMID: 20350812]
[7]
Aly, A.A.; El-Sheref, E.M.; Bakheet, M.E.M.; Mourad, M.A.E.; Brown, A.B.; Bräse, S.; Nieger, M.; Ibrahim, M.A.A. Bioorg. Chem., 2018, 81, 700-712.
[http://dx.doi.org/10.1016/j.bioorg.2018.09.017] [PMID: 30268050]
[8]
Haghjoo, A.H.R.; Moradi, R.E.O. J. Chem. Res., 2018, 42(2), 116-120.
[http://dx.doi.org/10.3184/174751918X15192990175864]
[9]
Watpade, R.; Bholay, A.; Toche, R.J.J. Heterocyclic Chem., 2017, 54(6), 3434-3439.
[http://dx.doi.org/10.1002/jhet.2966]
[10]
Khalafy, J.; Arlan, F.M.; Chalanchi, S.S. J. Heterocycl. Chem., 2018, 55(1), 149-153.
[http://dx.doi.org/10.1002/jhet.3017]
[11]
Fatma, S.; Bishnoi, A.; Verma, A.K.; Singh, R.; Srivastava, A. J. Mol. Struct., 2017, 1139, 338-352.
[http://dx.doi.org/10.1016/j.molstruc.2017.03.051]
[12]
Montagut-Romans, A.; Boulven, M.; Lemaire, M.; Popowycz, F. RSC Advances, 2016, 6(6), 4540-4544.
[http://dx.doi.org/10.1039/C5RA22440C]
[13]
Jun, J.V.; Petersson, E.J.; Chenoweth, D.M. J. Am. Chem. Soc., 2018, 140(30), 9486-9493.
[http://dx.doi.org/10.1021/jacs.8b03738] [PMID: 30028130]
[14]
Guillena, G.; Ramon, D.J.; Yus, M. Tetrahedron Asymmetry, 2007, 18(6), 693-700.
[http://dx.doi.org/10.1016/j.tetasy.2007.03.002]
[15]
Biggs-Houck, J.E.; Younai, A.; Shaw, J.T. Curr. Opin. Chem. Biol., 2010, 14(3), 371-382.
[http://dx.doi.org/10.1016/j.cbpa.2010.03.003] [PMID: 20392661]
[16]
Isambert, N. Sanchez Duque, Mdel.M.; Plaquevent, J.C.; Génisson, Y.; Rodriguez, J.; Constantieux, T. Chem. Soc. Rev., 2011, 40(3), 1347-1357.
[http://dx.doi.org/10.1039/C0CS00013B] [PMID: 20963207]
[17]
Dömling, A.; Wang, W.; Wang, K. Chem. Rev., 2012, 112(6), 3083-3135.
[http://dx.doi.org/10.1021/cr100233r] [PMID: 22435608]
[18]
Khan, M.M.; Yousuf, R.; Khan, S. RSC Advances, 2015, 5(71), 57883-57905.
[http://dx.doi.org/10.1039/C5RA08059B]
[19]
Climent, M.J.; Corma, A.; Iborra, S. RSC Advances, 2012, 2(1), 16-58.
[http://dx.doi.org/10.1039/C1RA00807B]
[20]
Graaff, C.; Ruijter, E.; Orru, R.V.A. Chem. Soc. Rev., 2012, 41(10), 3969-4009.
[http://dx.doi.org/10.1039/c2cs15361k] [PMID: 22546840]
[21]
Brauch, S.; van Berkel, S.S.; Westermann, B. Chem. Soc. Rev., 2013, 42(12), 4948-4962.
[http://dx.doi.org/10.1039/c3cs35505e] [PMID: 23426583]
[22]
Cioc, R.C.; Ruijter, E.; Orru, R.V.A. Green Chem., 2014, 16(6), 2958-2975.
[http://dx.doi.org/10.1039/C4GC00013G]
[23]
Singh, M.S.; Chowdhury, S. RSC Advances, 2012, 2(11), 4547-4592.
[http://dx.doi.org/10.1039/c2ra01056a]
[24]
Han, L.; Hu, X.; Zhou, Z. Polycycl. Aromat. Compd., 2017, 37(1), 73-80.
[http://dx.doi.org/10.1080/10406638.2015.1099551]
[25]
Tanaka, K.; Toda, F. Chem. Rev., 2000, 100(3), 1025-1074.
[http://dx.doi.org/10.1021/cr940089p] [PMID: 11749257]
[26]
Martins, M.A.P.; Frizzo, C.P.; Moreira, D.N.; Buriol, L.; Machado, P. Chem. Rev., 2009, 109(9), 4140-4182.
[http://dx.doi.org/10.1021/cr9001098] [PMID: 19737022]
[27]
Simon, M.O.; Li, C. J. Chem. Soc. Rev., 2012, 41(4), 1415-1427.
[http://dx.doi.org/10.1039/C1CS15222J]
[28]
Dallinger, D.; Kappe, C.O. Chem. Rev., 2007, 107(6), 2563-2591.
[http://dx.doi.org/10.1021/cr0509410] [PMID: 17451275]
[29]
Li, C.J.; Chen, L. Chem. Soc. Rev., 2006, 35(1), 68-82.
[http://dx.doi.org/10.1039/B507207G] [PMID: 16365643]

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