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Knoevenagel Condensation Reaction Using Ionic Liquid [ADPQ][CF3SO3] as Green and Reusable Catalyst
Corresponding Author(s) : Ruichang Gao
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
Knoevenagel condensation reaction of aromatic aldehydes with some active methylene compounds proceeded efficiently without solvent using ionic liquids as catalyst. The experimental results show that these ionic liquids have good catalytic activities to the Knoevenagel condensation with a wide range of reactant. The reactions are carried out in a few minutes with high yields. The ionic liquids can be recycled and reused for 4 times without noticeably decreasing the catalytic activity.
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- S. Zhao, X. Wang and L. Zhang, RSC Adv., 3, 11691 (2013); doi:10.1039/c3ra40809d.
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- F. Su, M. Antonietti and X. Wang, Catal. Sci. Technol., 2, 1005 (2012); doi:10.1039/c2cy00012a.
- Y. Peng, J.Y. Wang, J. Long and G.H. Liu, Catal. Commun., 15, 10 (2011); doi:10.1016/j.catcom.2011.08.004.
- X.W. You, H. Yu, M.G. Wang, J. Wu and Z.C. Shang, Lett. Org. Chem., 9, 19 (2012); doi:10.2174/157017812799303953.
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- W.L. Wong and K.Y. Wong, Can. J. Chem., 90, 1 (2012); doi:10.1139/v11-110.
- R.V. Hangarge, D.V. Jarikote and M.S. Shingare, Green Chem., 4, 266 (2002); doi:10.1039/b111634g.
- X. Xin, X. Guo, H. Duan, Y. Lin and H. Sun, Catal. Commun., 8, 115 (2007); doi:10.1016/j.catcom.2006.05.034.
- A. Alizadeh, M.M. Khodaei and A. Eshghi, J. Org. Chem., 75, 8295 (2010); doi:10.1021/jo101696z.
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- B.C. Ranu and R. Jana, Eur. J. Org. Chem., 3767 (2006); doi:10.1002/ejoc.200600335.
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References
S. Zhao, X. Wang and L. Zhang, RSC Adv., 3, 11691 (2013); doi:10.1039/c3ra40809d.
F. Bigi, L. Chesini, R. Maggi and G.J. Sartori, J. Org. Chem., 64, 1033 (1999); doi:10.1021/jo981794r.
L.F. Tietze and N. Rackelmann, Pure Appl. Chem., 76, 1967 (2004); doi:10.1351/pac200476111967.
Y. Zhang, Q. Dou, L. Dai, X. Wang and Y. Chen, RSC Adv., 2, 8979 (2012); doi:10.1039/c2ra21571c.
M. Zahouily, M. Salah, B. Bahlaouane, A. Rayadh, A. Houmam, E.A. Hamed and S. Sebti, Tetrahedron, 60, 1631 (2004); doi:10.1016/j.tet.2003.11.086.
N. Tavakoli-Hoseini, M.M. Heravi and F.F. Bamoharram, Asian J. Chem., 22, 7208 (2010).
M.B. Deshmukh, S. Patil, S.D. Jadhav and P.B. Pawar, Synth. Commun., 42, 1177 (2012); doi:10.1080/00397911.2010.537423.
G. Bartoli, M. Bosco, A. Carlone, R. Dalpozzo, P. Galzerano, P. Melchiorre and L. Sambri, Tetrahedron Lett., 49, 2555 (2008); doi:10.1016/j.tetlet.2008.02.093.
M. Venkatanarayana and P.K. Dubey, Heteroatom Chem., 23, 41 (2012); doi:10.1002/hc.20750.
F. Su, M. Antonietti and X. Wang, Catal. Sci. Technol., 2, 1005 (2012); doi:10.1039/c2cy00012a.
Y. Peng, J.Y. Wang, J. Long and G.H. Liu, Catal. Commun., 15, 10 (2011); doi:10.1016/j.catcom.2011.08.004.
X.W. You, H. Yu, M.G. Wang, J. Wu and Z.C. Shang, Lett. Org. Chem., 9, 19 (2012); doi:10.2174/157017812799303953.
A. Rahmati and K. Vakili, Amino Acids, 39, 911 (2010); doi:10.1007/s00726-010-0537-z.
S. Mallouk, K. Bougrin, A. Laghzizil and R. Benhida, Molecules, 15, 813 (2010); doi:10.3390/molecules15020813.
Q. Liu and H.M. Ai, Synth. Commun., 42, 3004 (2012); doi:10.1080/00397911.2011.574245.
W.L. Wong and K.Y. Wong, Can. J. Chem., 90, 1 (2012); doi:10.1139/v11-110.
R.V. Hangarge, D.V. Jarikote and M.S. Shingare, Green Chem., 4, 266 (2002); doi:10.1039/b111634g.
X. Xin, X. Guo, H. Duan, Y. Lin and H. Sun, Catal. Commun., 8, 115 (2007); doi:10.1016/j.catcom.2006.05.034.
A. Alizadeh, M.M. Khodaei and A. Eshghi, J. Org. Chem., 75, 8295 (2010); doi:10.1021/jo101696z.
A. Alizadeh, M.M. Khodaei and A. Eshghi, Can. J. Chem., 88, 514 (2010); doi:10.1139/V10-011.
B.C. Ranu and R. Jana, Eur. J. Org. Chem., 3767 (2006); doi:10.1002/ejoc.200600335.
H. Valizadeh and H. Gholipour, Synth. Commun., 40, 1477 (2010); doi:10.1080/00397910903097310.