Efficient method for Knoevenagel condensation in aqueous solution of amino acid ionic liquids (AAILs)

Ossowicz, Paula; Rozwadowski, Zbigniew; Gano, Marcin; Janus, Ewa

doi:10.1515/pjct-2016-0076

Abstract

This work reports on the use of the amino acid ionic liquids (AAILs) which have been used as catalysts in Knoevenagel condensation of various aldehydes with malononitrile. For research we use tetrabutylammonium ionic liquids based on eight natural amino acids. The reaction was carried out in an aqueous medium. Using water as solvent provided efficient and simple method of isolation of pure product with high yield. Moreover, amino acid ionic liquid dissolved in water could be reused many times without any loss of its catalytic activity. The influence of the anion was studied. Moreover the effect of technological parameters such as: the temperature, the catalyst content, and the reaction time on yield of reaction were investigated.

References

1. March, J. (1992). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (7th ed.). New York, USA: John Wiley & Sons.
Search in Google Scholar Back to article
2. Song, A., Wang, X. & Lam, K.S. (2003). A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum’s acid with ortho-hydroxyaryl aldehydes or ketones. Tetrahedron Lett. 44(9), 1755–1758. DOI:10.1016/S0040-4039(03)00108-4.10.1016/S0040-4039(03)00108-4
Search in Google Scholar Back to article
3. Bigi, F., Chesini, L., Maggi, R. & Sartori, G.J. (1999). Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids. J. Org. Chem. 64(3), 1033–1035. DOI: 10.1021/jo981794r.10.1021/jo981794r
Search in Google Scholar Back to article
4. Flachsmann, F. (2013). Fragrance compounds. U.S. Patent No. 8575386B2. Duebendorf C.H.: United States Patent Application.
Search in Google Scholar Back to article
5. Hoshino, M., Sugiyama, M., Kawamata, A., Joukura, H. & Imokawa, G. 1994. Naphtalenmethylenemalonic diesters and UV absorbers and cosmetic compositions containing the diesters. EU Pat. EP 663206A1.
Search in Google Scholar Back to article
6. Beutler, U., Fuenfschilling, P.C. & Steinkemper, A. (2007). An Improved Manufacturing Process for the Antimalaria Drug Coartem. Part II. Org. Process Res. Dev. 11(3), 341–343. DOI: 10.1021/op060244p.10.1021/op060244p
Search in Google Scholar Back to article
7. Martinez, C.A., Hu, S., Dumond, Y., Tao, J., Kelleher, P. & Tully, L. (2008). Development of a chemoenzymatic manufacturing process for pregabalin. Org. Process Res. Dev. 12(3), 392–398. DOI: 10.1021/op7002248.10.1021/op7002248
Search in Google Scholar Back to article
8. Walker, S.D., Borths, C.J., DiVirgilio, E., Huang, L., Liu, P., Morrison, H., Sugi, K., Tanaka, M., Woo, J.C.S. & Faul, M.M. (2011). Development of a scalable synthesis of a GPR40 receptor agonist. Org. Process Res. Dev. 15(3), 570–580. DOI: 10.1021/op1003055.10.1021/op1003055
Search in Google Scholar Back to article
9. Menegatti, R. (2012). Designing highly efficient solvents for the Knoevenagel condensation: two novel dicationic dimethyl phosphate ionic liquids. In: M. Kidwai & N.K. Mishra (Eds.), Green Chemistry – Environmentally Benign Approaches (pp. 13–32). Intech, Rijeka.
Search in Google Scholar Back to article
10. Anastas, P.T. & Warner, J.C. (1998). Green Chemistry: Theory and Practice (1st ed.). Oxford University Press, New York.
Search in Google Scholar Back to article
11. Anastas, P.T. & Kirchhoff, M.M. (2002). Origins, current status, and future challenges of green chemistry. Acc. Chem. Res. 35(9), 686–694. DOI: 10.1021/ar010065m.10.1021/ar010065m
Search in Google Scholar Back to article
12. Reddy, T.I. & Verma, R.S. (1997). Rare earth-exchanged NaY zeolite-promoted Knoevenagel condensation. Tetrahedron Lett. 38(10), 1721–1724. DOI: 10.1016/S0040-4039(97)00180-9.10.1016/S0040-4039(97)00180-9
Search in Google Scholar Back to article
13. McCluskey, A., Robinson, P.J., Hill, T., Scott, J.L. & Edwards, J.K. (2002). Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water and solvent free (dry grind) approaches. Tetrahedron Lett. 43(17), 3117–3120. DOI: 10.1016/S0040-4039(02)00480-X.10.1016/S0040-4039(02)00480-X
Search in Google Scholar Back to article
14. Bigi, F., Conforti, M.L., Maggi, R., Piccinno, A. & Sartori, G. (2000). Clean Synthesis in Water: Uncatalysed Preparation of Ylidenemalononitriles. Green Chem. 2, 101–103. DOI: 10.1039/B001246G.10.1039/b001246g
Search in Google Scholar Back to article
15. Gomes, M.N., de Oliveira, C.M.A., Garrote, C.F.D., de Oliveira, V. & Menegatti, R. (2011). Condensation of ethyl cyanoacetate with aromatic aldehydes in water, catalyzed by morpholine. Synth. Commun. 41(1), 52–57. DOI: 10.1080/00397910903531771.10.1080/00397910903531771
Search in Google Scholar Back to article
16. Mallouk, S., Bougrin, K., Laghzizil, A. & Benhida, R. (2010). Microwave-Assisted and Efficient Solvent-free Knoevenagel Condensation. A Sustainable Protocol Using Porous Calcium Hydroxyapatite as Catalyst. Molecules 15(2), 813–823. DOI: 10.3390/molecules15020813.10.3390/molecules15020813
Search in Google Scholar Back to article
17. Tahmassebi, D., Wilson, L.J.A. & Kieser, J.M. (2009). Knoevenagel Condensation of Aldehydes with Meldrum’s Acid in Ionic Liquids. Synth. Commun. 39(14), 2605–2613. DOI: 10.1080/00397910802663345.10.1080/00397910802663345
Search in Google Scholar Back to article
18. Otaibi, A.A., Gordon, C.P., Gilbert, J., Sakoff, J.A. & McCluskey, A. (2014), The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles. RSC Adv. 4, 19806–19813. DOI: 10.1039/c3ra47418f.10.1039/c3ra47418f
Search in Google Scholar Back to article
19. Morrison, D.W., Forbes, D.C. & Davis, Jr J.H. (2001). Base-promoted reactions in ionic liquid solvents. The Knoevenagel and Robinson annulation reactions. Tetrahedron Lett. 42(35), 6053–6055. DOI: 10.1016/S0040-4039(01)01228-X.10.1016/S0040-4039(01)01228-X
Search in Google Scholar Back to article
20. Suresh, J. & Sandhu, J. (2013). Ultrasound-assisted synthesis of 2,4-thiazolidinedione and rhodanine derivatives catalyzed by task-specific ionic liquid: [TMG][Lac]. Org. Med. Chem. Lett. 3:(2), 1–6. DOI: 10.1186/2191-2858-3-2.10.1186/2191-2858-3-2359950723458122
Search in Google Scholar Back to article
21. Moosavi-Zare, A.R., Zolfigol, M.A., Khaledian, O., Khakyzadeh, V., Farahani, M.D. & Kruger, H.G. (2014). Tandem Knoevenagel-Michael-cyclocondensation reactions of malononitrile, various aldehydes and dimedone using acetic acid functionalized ionic liquid. New J. Chem. 38, 2342–2347. DOI: 10.1039/C3NJ01509B.10.1039/c3nj01509b
Search in Google Scholar Back to article
22. Zhang, J., Zhang, Y. & Zhou, Z. (2014). Hydroxyl ammonium ionic liquid-catalyzed simple and efficient synthesis of 5-arylidene-2,4-thiazolidinediones under solvent-free conditions. Green Chem. Lett. Rev. 7(1), 90–94. DOI: 10.1080/17518253.2014.895866.10.1080/17518253.2014.895866
Search in Google Scholar Back to article
23. Ying, A., Ni, Y., Xu, S., Liu, S., Yang, J. & Li, R. (2014). Novel DABCO Based Ionic Liquids: Green and Efficient Catalysts with Dual Catalytic Roles for Aqueous Knoevenagel Condensation. Ind. Eng. Chem. Res. 53(14), 5678–5682. DOI: 10.1021/ie500440w.10.1021/ie500440w
Search in Google Scholar Back to article
24. Zhao, S., Wang, X. & Zhang, L. (2013). Rapid and efficient Knoevenagel condensation catalyzed by a novel protic ionic liquid under ultrasonic irradiation. RSC Adv. 3, 11691–11696. DOI: 10.1039/C3RA40809D.10.1039/c3ra40809d
Search in Google Scholar Back to article
25. Tzani, A., Douka, A., Papadopoulos, A., Pavlatou, E.A., Voutsas, E. & Detsi, A. (2013). Synthesis of Biscoumarins Using Recyclable and Biodegradable Task-Specific Ionic Liquids. ACS Sustainable Chem. Eng. 1(9), 1180–1185. DOI: 10.1021/sc4001093.10.1021/sc4001093
Search in Google Scholar Back to article
26. Siddiqui, Z.N. & Khan, K. (2014). [Et3NH][HSO4]-Catalyzed Efficient, Eco-Friendly, and Sustainable Synthesis of Quinoline Derivatives via Knoevenagel Condensation. ACS Sustainable Chem. Eng. 2(5), 1187–1194. DOI: 10.1021/sc500023q.10.1021/sc500023q
Search in Google Scholar Back to article
27. Hu, X., Zhang, B., Gao, Y. & Dong, S. (2014). Knoevenagel reactions catalyzed by ionic liquids. J. Chem. Pharm. Res. 6, 864–868. CODEN:JCPRC5 ISSN:0975-7384.
Search in Google Scholar Back to article
28. Zicmanis, A. & Anteina, L. (2014). Dialkylimidazolium dimethyl phosphates as solvents and catalysts for the Knoevenagel condensation reaction. Tetrahedron Lett. 55(12), 2027–2028. DOI: 10.1016/j.tetlet.2014.02.035.10.1016/j.tetlet.2014.02.035
Search in Google Scholar Back to article
29. Moriel, P., Garcia-Suarez, E.J., Martinez, M., Garcia, A.B., Montes-Moran, M.A., Calvino-Casilda, V. & Banares, M.A. (2010). Synthesis, characterization, and catalytic activity of ionic liquids based on biosources. Tetrahedron Lett. 51(37) 4877–4881. DOI: 10.1016/j.tetlet.2010.07.060.10.1016/j.tetlet.2010.07.060
Search in Google Scholar Back to article
30. Ouyang, F., Zhou, Y., Li, Z.M., Hu, N. & Tao, D.J. (2014). Tetrabutylphosphonium amino acid ionic liquids as efficient catalysts for solvent-free Knoevenagel condensation reactions. Korean J. Chem. Eng. 31(8), 1377–1383. DOI: 10.1007/s11814-014-0077-4.10.1007/s11814-014-0077-4
Search in Google Scholar Back to article
31. Fukumoto, K., Yoshizawa, M. & Ohno, H. (2005). Room Temperature Ionic Liquids from 20 Natural Amino Acids. J. Am. Chem. Soc. 127(8), 2398–2399. DOI: 10.1021/ja043451i.10.1021/ja043451i15724987
Search in Google Scholar Back to article
32. Allen, C.R., Richard, P.L., Ward, A.J., Van de Water, L.G.A., Masters, A.F. & Maschmeyer, T. (2006). Facile synthesis of ionic liquids possessing chiral carboxylates. Tetrahedron Lett. 47(41), 7367–7373. DOI: 10.1016/j.tetlet.2006.08.007.10.1016/j.tetlet.2006.08.007
Search in Google Scholar Back to article
33. Ossowicz, P., Janus, E., Schroeder, G. & Rozwadowski, Z. (2013). Spectroscopic studies of amino acid ionic liquid-supported Schiff bases. Molecules 18(5), 4986–5004. DOI: 10.3390/molecules18054986 18, 4986–5004.10.3390/molecules18054986626971023629755
Search in Google Scholar Back to article

Efficient method for Knoevenagel condensation in aqueous solution of amino acid ionic liquids (AAILs)

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