A Facile One-pot Synthesis of Substituted Quinolines via Cascade Friedlander Reaction from Isoxazoles with Ammonium Formate-Pd/C and Ketones

Author(s): Da Chen, Xuan Wang, Runnan Wang, Yao Zhan, Xiaohan Peng, Tian Xia, Zhenming Zhang, Runlai Li*, Shu'an Li*.

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 3 , 2020

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

The Friedlander reaction is the most commonly used method to synthesis substituted quinolines, the essential intermediates in the medicine industry. A facile one-pot approach for synthesizing substituted quinolines by the reaction of isoxazoles, ammonium formate-Pd/C, concentrated sulfuric acid, methanol and ketones using Friedlander reaction conditions is reported. Procedures for the synthesis of quinoline derivatives were optimized, and the yield was up to 90.4%. The yield of aromatic ketones bearing electron-withdrawing groups was better than the ones with electron-donating substituents. The structures of eight substituted quinolines were characterized by MS, IR, H-NMR and 13CNMR, which were in agreement with the expected structures. The mechanism for the conversion was proposed, which involved the Pd/C catalytic hydrogen transfer reduction of unsaturated five-membered ring of isoxazole to produce ortho-amino aromatic ketones. Then the nucleophilic addition of with carbonyl of the ketones generated Schiff base in situ, which underwent an intermolecular aldol reaction followed by the elimination of H2O to give production of substituted quinolines. This new strategy can be readily applied for the construction of quinolines utilizing a diverse range of ketones and avoids the post-reaction separation of the o-amino aromatic ketone compounds. The conventionally used o-amino aromatic ketone compounds in Friedlander reaction to prepare substituted quinoline are laborious to synthesize and are apt to self-polymerize. While oxazole adopted in this work can be prepared at ease by the condensation of benzoacetonitrile and nitrobenzene derivatives under the catalysis of a strong base. Moreover, the key features of this protocol are readily available starting materials, excellent functional group tolerance, mild reaction conditions, operational simplicity, and feasibility for scaling up.

Keywords: Isoxazoles, Friedlander reaction, quinolines, one-pot synthesis, ammonium formate, ketones.

[1]
Eswaran, S.; Adhikari, A.V.; Shetty, N.S. Eur. J. Med. Chem., 2009, 44(11), 4637-4647.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.031] [PMID: 19647905]
[2]
Krishnakumar, V.; Khan, F.R.N.; Mandal, B.K.; Mitta, S.; Dhasamandha, R.; Govindan, V.R. Res. Chem. Intermed., 2012, 38, 1819-1826.
[http://dx.doi.org/10.1007/s11164-012-0505-1]
[3]
Kaur, K.; Jain, M.; Reddy, R.P.; Jain, R. Eur. J. Med. Chem., 2010, 45(8), 3245-3264.
[http://dx.doi.org/10.1016/j.ejmech.2010.04.011] [PMID: 20466465]
[4]
Biamonte, M.A.; Wanner, J.; Le Roch, K.G. Bioorg. Med. Chem. Lett., 2013, 23(10), 2829-2843.
[http://dx.doi.org/10.1016/j.bmcl.2013.03.067] [PMID: 23587422]
[5]
Vandekerckhove, S.; D’hooghe, M. Bioorg. Med. Chem. Lett., 2015, 23, 5098-5119.
[http://dx.doi.org/10.1016/j.bmc.2014.12.018]
[6]
Patel, S.R.; Gangwal, R.; Sangamwar, A.T.; Jain, R. Eur. J. Med. Chem., 2015, 93, 511-522.
[http://dx.doi.org/10.1016/j.ejmech.2015.02.034] [PMID: 25747550]
[7]
Bedoya, L.M.; Abad, M.J.; Calonge, E.; Saavedra, L.A.; Gutierrez, C. M.; Kouznetsov, V.V.; Alcami, J.; Bermejo, P.; Bermejo, P. Antiviral Res., 2010, 87(3), 338-344.
[http://dx.doi.org/10.1016/j.antiviral.2010.06.006] [PMID: 20600334]
[8]
Musiol, R. Curr. Pharm. Des., 2013, 19(10), 1835-1849.
[http://dx.doi.org/10.2174/1381612811319100008] [PMID: 23092281]
[9]
Heiniger, B.; Gakhar, G.; Prasain, K.; Hua, D.H.; Nguyen, T.A. Anticancer Res., 2010, 30(10), 3927-3932.
[PMID: 21036704]
[10]
Afzal, O.; Kumar, S.; Haider, M.R.; Ali, M.R.; Kumar, R.; Jaggi, M.; Bawa, S. Eur. J. Med. Chem., 2015, 97, 871-910.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.044] [PMID: 25073919]
[11]
Chung, P.Y.; Bian, Z.X.; Pun, H.Y.; Chan, D.; Chan, A.S.C.; Chui, C.H.; Tang, J.C.O.; Lam, K.H. Future Med.Chem.,, 2015, 7-, 947-967.
[12]
Sloop, J.C. J. Phys. Org. Chem., 2009, 22, 110-117.
[http://dx.doi.org/10.1002/poc.1433]
[13]
Brouet, J.C.; Gu, S.; Peet, N.P.; Williams, J.D. Synth. Commun., 2009, 39, 1563-1569.
[http://dx.doi.org/10.1080/00397910802542044]
[14]
Theoclitou, M.E.; Robinson, L.A. Tetrahedron Lett., 2002, 43, 3907-3910.
[http://dx.doi.org/10.1016/S0040-4039(02)00614-7]
[15]
Ivachtchenko, A.V.; Khvat, A.V.; Kobak, V.V.; Kysil, V.M.; Williams, C.T. Tetrahedron Lett., 2004, 45, 5473-5476.
[http://dx.doi.org/10.1016/j.tetlet.2004.05.028]
[16]
Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A. Carreiras, Mdo.C.; Soriano, E. Chem. Rev., 2009, 109(6), 2652-2671.
[http://dx.doi.org/10.1021/cr800482c] [PMID: 19361199]
[17]
Muchowski, J.M.; Maddox, M.L. Can. J. Chem., 2004, 82(3), 461-478.
[http://dx.doi.org/10.1139/v03-211]
[18]
Li, B.; Guo, C.; Fan, X.; Zhang, J.; Zhang, X. Tetrahedron Lett., 2014, 55, 5944-5948.
[http://dx.doi.org/10.1016/j.tetlet.2014.09.024]
[19]
Davis, R.B.; Pizzini, L.C. J. Org. Chem., 1960, 25(11), 1884-1888.
[http://dx.doi.org/10.1021/jo01081a015]
[20]
Maguire, M.P.; Sheets, K.R.; McVety, K.; Spada, A.P.; Zilberstein, A. J. Med. Chem., 1994, 37(14), 2129-2137.
[http://dx.doi.org/10.1021/jm00040a003] [PMID: 8035419]
[21]
Yadav, J.S.; Rao, P.P.; Sreenu, D.; Rao, R.S.; Kumar, V.N.; Nagaiah, K.; Prasad, A.R. Tetrahedron Lett., 2005, 46, 7249-7253.
[http://dx.doi.org/10.1016/j.tetlet.2005.08.042]
[22]
Arumugam, P.; Karthikeyan, G.; Atchudan, R.; Muralidharan, D.; Perumal, P.T. Chem. Lett., 2005, 34, 314-315.
[http://dx.doi.org/10.1246/cl.2005.314]
[23]
Yadav, J.S.; Reddy, B.S.; Sreedhar, P.; Rao, R.S.; Nagaiah, K. Synthesis, 2004, 2381-2385.
[http://dx.doi.org/10.1055/s-2004-831185]
[24]
Teimouri, A.; Chermahini, A.N. Arab. J. Chem., 2016, 9, S433-S439.
[http://dx.doi.org/10.1016/j.arabjc.2011.05.018]
[25]
Fan, X.; Zhang, Y. Tetrahedron Lett., 2002, 43, 7001-7003.
[http://dx.doi.org/10.1016/S0040-4039(02)01583-6]
[26]
Palimkar, S.S.; Siddiqui, S.A.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. J. Org. Chem., 2003, 68(24), 9371-9378.
[http://dx.doi.org/10.1021/jo035153u] [PMID: 14629159]
[27]
Fehnel, E.A. J. Org. Chem., 1966, 31(9), 2899-2902.
[http://dx.doi.org/10.1021/jo01347a038] [PMID: 5919934]


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 3
Year: 2020
Page: [211 - 215]
Pages: 5
DOI: 10.2174/1570178616666190618091617
Price: $65

Article Metrics

PDF: 18
HTML: 1