Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

[Bmim][CF3COO] as a Solvent and a Catalyst for the Knoevenagel Condensation

Author(s): Nguyen Thi Chung, Vo Cong Dung and Dau Xuan Duc*

Volume 21, Issue 10, 2024

Published on: 14 March, 2024

Page: [883 - 888] Pages: 6

DOI: 10.2174/0115701786294320240311022937

Price: $65

Abstract

A facile and green strategy for the Knoevenagel condensation reaction of aryl aldehydes and active methylene compounds using [Bmim][CF3COO] ionic liquid as a solvent and a catalyst has been introduced. The method features some advantages such as good to excellent yield of products, relatively short reaction time, mild reaction conditions, broad substrate scope, and scalability. Moreover, the ionic liquid solvent could be conveniently recycled and reused up to three times without any considerable loss of catalytic activity. Twelve products were obtained in high yields, and their structures were confirmed by NMR data. A plausible reaction mechanism involving the role of the ionic liquid catalyst was also suggested.

Keywords: Ionic liquid, methylene compounds, ethyl cyanoacetate, malonitrile, diethyl malonate, benzaldehyde.

« Previous Next »
Graphical Abstract

[1]
van Beurden, K.; de Koning, S.; Molendijk, D.; van Schijndel, J. Green Chem. Lett. Rev., 2020, 13(4), 349-364.
[http://dx.doi.org/10.1080/17518253.2020.1851398]
[2]
Vekariya, R.H.; Patel, H.D. Synth. Commun., 2014, 44(19), 2756-2788.
[http://dx.doi.org/10.1080/00397911.2014.926374]
[3]
Tietze, L.F. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
[4]
Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F. Tetrahedron, 1994, 50(39), 11499-11508.
[http://dx.doi.org/10.1016/S0040-4020(01)89287-5]
[5]
Gómez, R.; Segura, J.L.; Martín, N. Chem. Commun. (Camb.), 1999, (7), 619-620.
[http://dx.doi.org/10.1039/a809405e]
[6]
Segura, J.L.; Martín, N.; Hanack, M. Eur. J. Org. Chem., 1999, 1999(3), 643-651.
[http://dx.doi.org/10.1002/(SICI)1099-0690(199903)1999:3<643:AID-EJOC643>3.0.CO;2-V]
[7]
Turpaev, K.; Ermolenko, M.; Cresteil, T.; Drapier, J.C. Biochem. Pharmacol., 2011, 82(5), 535-547.
[http://dx.doi.org/10.1016/j.bcp.2011.05.028] [PMID: 21669191]
[8]
Turpaev, K.; Drapier, J.C. Eur. J. Pharmacol., 2009, 606(1-3), 1-8.
[http://dx.doi.org/10.1016/j.ejphar.2009.01.015] [PMID: 19374863]
[9]
Ghorbani, M.; Noura, S.; Oftadeh, M.; Zolfigol, M.A.; Soleimani, M.H.; Behbodi, K. J. Mol. Liq., 2015, 212, 291-300.
[http://dx.doi.org/10.1016/j.molliq.2015.09.024]
[10]
Park, J.H.; Lee, Y.R.; Kim, S.H. Tetrahedron, 2013, 69(46), 9682-9689.
[http://dx.doi.org/10.1016/j.tet.2013.09.021]
[11]
Bose, D.S.; Narsaiah, A.V. J. Chem. Res., 2001, 2001(46), 36-38.
[12]
Narsaiah, A.V.; Basak, A.K.; Visali, B.; Nagaiah, K. Synth. Commun., 2004, 34(16), 2893-2901.
[http://dx.doi.org/10.1081/SCC-200026625]
[13]
Lehnert, W. Tetrahedron, 1974, 30(2), 301-305.
[http://dx.doi.org/10.1016/S0040-4020(01)91461-9]
[14]
Shanthan Rao, P.; Venkataratnam, R.V. Tetrahedron Lett., 1991, 32(41), 5821-5822.
[http://dx.doi.org/10.1016/S0040-4039(00)93564-0]
[15]
Bartoli, G.; Beleggia, R.; Giuli, S.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Paoletti, M. Tetrahedron Lett., 2006, 47(37), 6501-6504.
[http://dx.doi.org/10.1016/j.tetlet.2006.07.031]
[16]
Leelavathi, P.; Kumar, S. J. Mol. Catal. Chem., 2005, 240, 99-102.
[http://dx.doi.org/10.1016/j.molcata.2005.06.026]
[17]
Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Galzerano, P.; Melchiorre, P.; Sambri, L. Tetrahedron Lett., 2008, 49(16), 2555-2557.
[http://dx.doi.org/10.1016/j.tetlet.2008.02.093]
[18]
Bao, W.; Zhang, Y.; Wang, J. J. Synth. Commun., 1996, 26(16), 3025-3028.
[http://dx.doi.org/10.1080/00397919608004607]
[19]
Liu, S.; Ni, Y.; Yang, J.; Hu, H.; Ying, A.; Xu, S. Chin. J. Chem., 2014, 32(4), 343-348.
[http://dx.doi.org/10.1002/cjoc.201400025]
[20]
Roy, B.; Roy, A.S.; Panda, A.B.; Islam, S.M.; Chattopadhyay, A.P. ChemistrySelect, 2016, 1(15), 4778-4784.
[http://dx.doi.org/10.1002/slct.201600380]
[21]
Hu, Y.; Yao, N.; Tan, J.; Liu, Y. Synlett, 2019, 30(6), 699-702.
[http://dx.doi.org/10.1055/s-0037-1612076]
[22]
Fu, Z.; Tan, Y.; Zhang, J.; Liao, S.; Su, D.; Chen, H.; Yu, Y. Peng, J. Inorg. Chem. Commun., 2012, 15, 221-224.
[http://dx.doi.org/10.1016/j.inoche.2011.10.031]
[23]
Panchenko, V.N.; Matrosova, M.M.; Jeon, J.; Jun, J.W.; Timofeeva, M.N.; Jhung, S.H. J. Catal., 2014, 316, 251-259.
[http://dx.doi.org/10.1016/j.jcat.2014.05.018]
[24]
Yang, Y.; Yao, H.F.; Xi, F.G.; Gao, E.Q. J. Mol. Catal. Chem., 2014, 390, 198-205.
[http://dx.doi.org/10.1016/j.molcata.2014.04.002]
[25]
Taher, A.; Lumbiny, B.J.; Lee, I.M. Inorg. Chem. Commun., 2020, 119108092
[http://dx.doi.org/10.1016/j.inoche.2020.108092]
[26]
Karchgaudhuri, N.; De, A.; Mitra, A.K. J. Chem. Res., 2002, 2002, 180-183.
[27]
Steinrück, H.P.; Wasserscheid, P. Catal. Lett., 2015, 145(1), 380-397.
[http://dx.doi.org/10.1007/s10562-014-1435-x]
[28]
Duc, D.X.; Chung, N.T. Lett. Org. Chem., 2023, 20(8), 689-695.
[http://dx.doi.org/10.2174/1570178620666230207093953]
[29]
Duc, D.X. Curr. Organocatal., 2023, 10(1), 66-72.
[http://dx.doi.org/10.2174/2213337210666221214121957]
[30]
Morrison, D.W.; Forbes, D.C.; Davis, J.H., Jr Tetrahedron Lett., 2001, 42(35), 6053-6055.
[http://dx.doi.org/10.1016/S0040-4039(01)01228-X]
[31]
Harjani, J.R.; Nara, S.J.; Salunkhe, M.M. Tetrahedron Lett., 2002, 43(6), 1127-1130.
[http://dx.doi.org/10.1016/S0040-4039(01)02341-3]
[32]
Tahmassebi, D.; Wilson, L.J.A.; Kieser, J.M. Synth. Commun., 2009, 39(14), 2605-2613.
[http://dx.doi.org/10.1080/00397910802663345]
[33]
Xin, X.; Guo, X.; Duan, H.; Lin, Y.; Sun, H. Catal. Commun., 2007, 8(2), 115-117.
[http://dx.doi.org/10.1016/j.catcom.2006.05.034]
[34]
Mulla, S.A.R.; Sudalai, A.; Pathan, M.Y.; Siddique, S.A.; Inamdar, S.M.; Chavan, S.S.; Reddy, R.S. RSC Advances, 2012, 2(8), 3525-3529.
[http://dx.doi.org/10.1039/c2ra00849a]
[35]
Ranu, B.C.; Jana, R. Eur. J. Org. Chem., 2006, 2006(16), 3767-3770.
[http://dx.doi.org/10.1002/ejoc.200600335]
[36]
Hou, H.; Li, Z.; Ying, A.; Xu, S. Youji Huaxue, 2014, 34(7), 1277-1287.
[http://dx.doi.org/10.6023/cjoc201402021]
[37]
Pillai, M.K.; Singh, S.; Jonnalagadda, S.B. Synth. Commun., 2010, 40(24), 3710-3715.
[http://dx.doi.org/10.1080/00397910903531714]
[38]
Yang, X.C.; Jiang, H.; Ye, W. Synth. Commun., 2012, 42(3), 309-312.
[http://dx.doi.org/10.1080/00397911.2010.523858]
[39]
Zhou, Z.; Sun, Y. Synth. Commun., 2011, 41(21), 3162-3168.
[http://dx.doi.org/10.1080/00397911.2010.517376]
[40]
Jain, K.; Chaudhuri, S.; Pal, K.; Das, K. New J. Chem., 2019, 43(3), 1299-1304.
[http://dx.doi.org/10.1039/C8NJ04219E]
[41]
Rupanawar, B.D.; Veetil, S.M.; Suryavanshi, G. Eur. J. Org. Chem., 2019, 2019(36), 6232-6239.
[http://dx.doi.org/10.1002/ejoc.201900970]
[42]
Panja, S.K.; Dwivedi, N.; Saha, S. RSC Advances, 2015, 5(80), 65526-65531.
[http://dx.doi.org/10.1039/C5RA09036A]
[43]
Ghosh, S.; Jana, C.K. Org. Biomol. Chem., 2019, 17(48), 10153-10157.
[http://dx.doi.org/10.1039/C9OB02163A] [PMID: 31774427]
[44]
Kaumanns, O.; Lucius, R.; Mayr, H. Chemistry, 2008, 14(31), 9675-9682.
[http://dx.doi.org/10.1002/chem.200801277] [PMID: 18792024]

Rights & Permissions Print Cite
Article Metrics
16
1
Wayfinder Image
© 2024 Bentham Science Publishers | Privacy Policy