Facile synthesis of dihydropyrimidinone derivatives via Biginelli reaction using Brønsted acidic ionic liquid [H-NMP]+[CH3SO3]- as an efficient homogeneous catalyst

Iranian Journal of Catalysis

مقاله 2، دوره 8، شماره 4، اسفند 2018، صفحه 249-255   

نوع مقاله: Articles

نویسندگان

Hossein Naeimi^* ؛ Zahra Sadat Nazifi

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317-51167, I.R. Iran.

چکیده

In this research, a green, operationally simple, highly efficient and facile cascade Biginelli reaction using various aromatic aldehydes, ethyl acetoacetate, and urea/thiourea has been developed. First, the ionic liquid was prepared from the reaction of 1-methyl-2-pyrolidone with methane sulfonic acid. Then, this ionic liquid was applied as an acidic catalyst in the synthesis of dihydropyrimidinones as a target product under mild conditions. The ionic liquid and resulting products were characterized by physical and spectral data such as melting point, IR, ¹HNMR and ¹³CNMR. The significant advantages of this protocol are short reaction time, excellent yields and easily available starting materials.

کلیدواژه‌ها

Aldehyde؛ Thiourea؛ Dihydropyrimidinone؛ Ionic Liquid؛ Catalyst

مراجع

[1] G.C. Rovnyak, K. Atwal, A. Hedberg, S. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, M.F. Malley, J. Med. Chem. 35 (1992) 3254-3263.
[2] H. Cho, M. Ueda, K. Shima, A. Mizuno, Hayashimatsu, M. Ohnaka, Y. Takeuchi, Y. Hamaguchi, M.K. Aisaka, T. Hidaka, M. Kawai, M. Takeda, T. Ishihara, K. Funahashi, F. Satoh, M. Morita, T. Noguchi, J. Med. Chem. 32 (1989) 2396-2402.
[3] T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, Chem. Biol. 7 (2000) 275-286.
[4] K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, B.C. O’Reilly, J. Med. Chem. 34 (1991) 806-811.
[5] G.J. Grover, S. Dzwonczyk, D.M. McMullen, D.E. Normandin, C.S. Parham, P.G. Sleph, S. Moreland, J. Cardiovasc. Pharmacol. 26 (1995) 289-294.
[6] T. Matsuda, I. Hirao, Nippon Kagaku Zasshi 86 (1965) 1195-1199.
[7] E.W. Hurst, R. Hull, J. Med. Pharm. Chem. 3 (1961) 215-229.
[8] C.O. Kappe, A. Stadler, Org. React. 63 (2004) 1-116.
[9] L.Z. Gong, X.H. Chen, X.Y. Xu, Chem. Eur. J. 13 (2007) 8920-8926.
[10] P. Biginelli, Gazz. Chim. Ital., 23 (1893) 360-416. K. Folkers, H.J. Harwood, T.B. Johnson, J. Am. Chem. Soc. 54 (1932) 3751-3758.
[11] L. Moradi, G.R. Najafi, H. Saeidiroshan, Iran. J. Catal. 5 (2015) 357-364.
[12] S. Sayyahi, M. Behvandi, Iran. J. Catal. 5 (2015) 119-122.
[13] S. R. Jetti, D. Verma, S. Jain, Iran. J. Catal. 3 (2013) 203-209.
[14] I. Garcia-Saez, S. DeBonis, R. Lopez, F. Trucco, B. Rousseau, P. Thuery, F. Kozielski, J. Biol. Chem. 282 (2007) 9740-9747.
[15] C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043-1052.
[16] X.Y. Han, F. Xu, Y.Q. Luo, Q. Shen, Eur. J. Org. Chem. (2005) 1500-1503.
[17] J.C. Legeay, J.J. VandenEynde, J.P. Bazureau, Tetrahedron, 61 (2005) 12386-12397.
[18] B.L. Nilsson, L.E. Overman, J. Org. Chem. 71 (2006) 7706-7714.
[19] I. Cepanec, M.F.L.M. Litvic, I. Grungold, Tetrahedron, 63 (2007) 11822-11827.
[20] J. P. Wan, Y.J. Pan, Chem. Commun. 19 (2009) 2768-2770.
[21] T. Welton, Chem. Rev. 99 (1999) 2071-2084.
[22] H. Naeimi, Z.S. Nazifi, J. Ind. Eng. Chem. 20 (2013) 1043-1049.
[23] H. Naeimi, Z.S. Nazifi J. Chin. Chem. Soc. 60 (2013) 1113-1117.
[24] N. Isambert, M.D.M.S. Duque, J.C. Plaquevent, Y.G. Nisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40 (2011) 1347-1357.
[25] X. Tong, Y. Li, ChemSusChem 3 (2010) 350-355
[26] F.L. Zumpe, M. Flu, K. Schmitz, A. Lender, Tetrahedron Lett. 48 (2007) 1421-1423.
[27] Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 65 (2000) 3864-3868.
[28] S. Zhang, Z.C. Zhang, Green Chem. 4 (2002) 376-379.
[29] D. Elhamifar, F. Hosseinpoor, B. Karimi, S. Hajati, Microporous Mesoporous Mat. 204 (2015) 269-275.
[30] F. Dong, L. Jun, Z. Xinli, Y. Zhiwen, L. Zuliang, J. Mol. Catal. A: Chem. 274 (2007) 208-211.
[31] F. Heidarizadeh, E. Rezaee Nezhad, S. Sajjadifar, Sci. Iran. C 20 (2013) 561-565.
[32] F. Tamaddon, S. Moradi, J. Mol. Catal. A: Chem. 370 (2013) 117–122.
[33] R. Tayebee, M.M. Amini, M. Ghadamgahi, M. Armaghan, J. Mol. Catal. A: Chem. 366 (2013) 266- 274.
[34] H.G.O. Alvim, E.N. da Silva Júnior, B.A.D. Neto, RSC Adv. 4 (2014) 54282-54299.
[35] L.M. Ramos, B.C. Guido, C.C. Nobrega, J.R. Corrêa, R.G. Silva, H.C.B. de Oliveira, A.F. Gomes, F.C. Gozzo, B.A.D. Neto, Chem. Eur. J. 19 (2013) 4156-4168.