New Method for the Synthesis of 1-Methylimidazolium Trifluoroacetate and Its Application in Biginelli Reaction

DOI: 10.4236/gsc.2013.34A003   PDF   HTML     3,493 Downloads   5,130 Views   Citations


A new method for the synthesis of 1-methylimidazolium trifluoroacetate ([Hmi]Tfa), a protic ionic liquid (PIL), under ultrasonic irradiation has been developed. In addition, the product [Hmi]Tfa was successfully employed as solvent and catalyst in Biginelli reaction to prepare 3,4-dihydropyrimidinones (DHPMs) in high yield under mild reaction conditions.

Share and Cite:

K. M. Hua and T. N. Le, "New Method for the Synthesis of 1-Methylimidazolium Trifluoroacetate and Its Application in Biginelli Reaction," Green and Sustainable Chemistry, Vol. 3 No. 4A, 2013, pp. 14-17. doi: 10.4236/gsc.2013.34A003.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] H. Olivier-Bourbigou, L. Magna and D. Morvan, “Ionic Liquids and Catalysis: Recent Progess from Knowledge to Applications,” Applied Catalysis A: General, Vol. 373, No. 1-2, 2009, pp. 1-56.
[2] S. Zhang, N. Sun, X. He, X. Lu and X. Zhang, “Physical Properties of Ionic Liquids: Database and Evaluation,” Journal of Physical and Chemical Reference Data, Vol. 35, No. 4, 2006, pp. 1475-1517.
[3] N. Jain, A. Kumar, S. Chauhan and S. M. S. Chauhan, “Chemical and Biochemical Transformations in Ionic Liquids,” Tetrahedron, Vol. 61, No. 5, 2004, pp. 1015-1560.
[4] L. G. Tamar and J. D. Calum, “Protic Ionic liquids: Properties and Applications,” Chemical Reviews, Vol. 108, No. 1, 2008, pp. 206-237.
[5] D. S. Bose, M. Sudharshan and W. C. Sanjay, “New Protocol for Biginelli—A Practical Synthesic of Monastrol,” Arkivoc, 3, 2005, pp. 228-236.
[6] M. A. A. Abdulkarim and G. M. Nareruddin, “An Ultrasonic Assisted Mutilcomponent Reaction for Synthesic of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Con- dition,” Journal of Chemical and Pharmaceutical Research, Vol. 2, No. 3, 2010, pp. 536-543.
[7] Y.-X. Li and W. L. Bao, “Microwave-Assisted Solventless Biginelli Reaction Catalyzed by Montmorillonite Clay-SmCl3?6H2O System,” Chinese Chemical Letters, Vol. 14, No. 10, 2003, pp. 993-995.
[8] S. F. Fabio and C. O. Kappe, “The Biginelli Dihydropyrimidone Synthesis Using Polyphosphate Ester as a Mild and Efficient Cyclocondensation/Dehydration Reagent,” Arkivoc, Vol. 2001, No. 2, 2001, pp. 122-134.
[9] D. Russowsky, F. S. C. Romulo, A. A. S. Sergio, G. M. D. Marcelo, A. Fatima, A. P. Ronaldo, K. K. Luciana, A. A. Marcia and J. E. Carvalho, “Synthesis and Differential Antiproliferative Activity of Biginelli Reaction Compounds againts Cencer Cell Lines: Monastrol, Oxo-Monastrol and Oxygenated Analogues,” Bioorganic Chemistry, Vol. 34, No. 4, 2006, pp. 173-182.
[10] F. S. C. Romulo, A. Bernardi, O. B. A. Maria, D. Rus- sowsky and V. L. Eifler-Lima, “Synthesis of Dihydro-pyrimidin-2-one/thione Library and Cytotoxic Activity Against the Human U138-MG and Rat C6 Glioma Cell Lines,” Journal of the Brazilian Chemical Society, Vol. 22, No. 7, 2011, pp. 1379-1388.
[11] A. Mobinikhaledi and M. Kalhor, “Synthesis and Bio-logical Activity of Some Oxo-and Thioxopyridines,” International Journal of Drug Development and Research, Vol. 2, No. 1, 2010, pp. 68-272.,%20no.%205.pdf
[12] M. Adib, K. Ghanbary, M. Mostofi and M. R. Ganjali, “Efficient Ce(NO3)3?6H2O-Catalyzed Solvent-Free Synthesis for 3,4-Dihydropyrimidin-2(1H)-ones,” Molecules, Vol. 11, No. 8, 2006, pp. 649-654.
[13] K. K. Pasunooti, H. Chai, C. N. Jensen, B. K. Gorityala, S. Wang and X. W. Liu, “A Microwave-Assisted, Copper-Catalyzed Three-Component Synthesis of Dihydropyri- midinones under Mild Conditions,” Tetrahedron Letters, Vol. 52, No. 1, 2011, pp. 80-84.
[14] C. R. Brindadan, A. Hajra and U. Jana, “Indium(III) Chloride-Catalyzed One-Pot Synthesis of Dihydropyrimidinones by a Three-Component Coupling of 1,3-Dicar- bonyl Compounds, Aldehides, and Ure: An Improved Procedure or the Biginelli Reaction,” The Journal of Organic Chemistry, Vol. 65, No. 19, 2000, pp. 6270-6272.
[15] 15. A. Shaabani, A. Bazgir and F. Teimouri, “Ammonium Chloride-Catalyzed One-Pot Synthesis of 3,4-Dihydro- pyrimidin-2-(1H)-ones under Solvent-Free Conditions,” Tetrahedron Letters, Vol. 44, No. 4, 2003, pp. 857-859.
[16] M. Nasr-Esfahani and A. R. Khosropour, “An Efficient and Clean One-Pot Synthesis of 3,4-Dihydropyrimidine-2-(1H)-ones Catalyzed by SrCl2?6H2O-HCl in Solvent or Solvent-Free Conditions,” Bulletin of the Korean Chemical Society, Vol. 26, No. 9, 2005, pp. 1331-1332.
[17] C. Jiang and Q. D. You, “An Efficient and Solvent-Free One-Pot Synthesis of Dihydropyrimidionnes under Microwave Irradiation,” Chinese Chemical Letters, Vol. 18, No. 6, 2007, pp. 647-650.
[18] 18. F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, “A Revision of the Biginelli Reaction under Solid Acid Catalysis. Solvent-Free Synthesis of Dihydropyrimidines over Montmorillonite KSF,” Tetrahedron Letters, Vol. 40, No. 19, 1999, pp. 3465-3468.
[19] H. Lin, J. Ding, X. Chen and Z. Zhang, “An Efficient Synthesis of 3-Alkoxycarbonyl-4-aryl-3,4-dihydro-pyrimidin-2(1H)-ones Catalyzed by KSF Montmorillonite,” Molecules, Vol. 5, No. 12, 2000, pp. 1240-1243.
[20] V. R. Rani, N. Srinivas, M. R. Kishan, S. J. Kulkarni and K. V. Raghavan, “Zeolite-Catalyzed Cyclocondensation Reaction for the Selective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones,” Green Chemistry, Vol. 3, No. 6, 2001, pp. 305-306.

comments powered by Disqus

Copyright © 2020 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.