Bronsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Multi-Component Solvent-Free Synthesis of Dihydropyrimidinones
الموضوعات : International Journal of Heterocyclic Chemistry
Heshmatollah Alinezhad
1
(Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran)
Neda Ghobadi
2
(Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran)
الکلمات المفتاحية: thiourea, Ionic liquid, reusable catalyst, Dihydropyrimidinone, Brønsted acidic,
ملخص المقالة :
An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones by condensation of 1,3-dicarbonyl compounds, Aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amount of Brønsted acidic ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} under thermal solvent-free conditions reacted easily to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones and thiones. Straightforward and clean workup, short reaction time, good to excellent yields and reusability of the catalyst are the advantages of this method
[1] (a) J. M. Nuss and P. A. Renhowe, “Advances in solid-supported organic synthesis methods”, Curr Opin Drug Discov Devel, 1999, 2, 631-650. (b) S. F. Oliver and C. Abell, “Combinatorial synthetic design”, Current Opinion in Chemical Biology, 1999, 3, 299-306. (c) L.A. Thompson and J.A. Ellman, Chemical Reviews, 1996, 96, 555.
[2] (a) B. B. Snider and Z. Shi, “Biomimetic synthesis of (+)-crambines A, B, C1, and C2 Revision of the structure of crambines B and C1, The Journal of Organic Chemistry, 1993, 58, 3828 (b) C. O Kappe, European Journal of Medicinal Chemistry, 2000, 12, 1043 (c) C. O. Kappe, QSAR & Combinatorial Science, 2003, 22, 630.
[3] G. C. Rovnyak, S. D. Kimball, B. Beyer et al., Journal of Medical Chemistry, 1995, 38, 119.
[4] (a) C. O. Kappe, W. M. F. Fabian, and, M. A. Semones, Tetrahedron, 1997, 53, 2803. (b) J. C. Barrow, P. G. Nantermet, H. G. Selnick, Journal of Medical Chemistry, 2000, 43, 2703.
[5] J. S. Yadav, B. V. Subba Reddy, K. Bhaskar Reddy, K. Sarita Raj ,A. R. Prasad, Journal of the Chemical Society, Perkin Transactions 1, 2001, 16, 1939.
[6] B. B. Snider; J. Chen, A. D. Patil, and A. Freyer, Tetrahedron Letters, 1996, 37, 6977.
[7] P. Biginelli, GazzettaChimicaItaliana, 1893, 23, 360.
[8] N. Y. Fu, Y. F. Yuan, Z. Cao, Tetrahedron, 2000, 58, 4801.
[9] (a) J. Jiang, J. Yu, X. Sun, Angewandte Chemie International Edition 2008, 47, 2458. (b) H. Khabazzadeh, K. Saidi, H. Sheibani, Bioorganic & Medicinal Chemistry Letters 2008, 18, 278. (c) R. Varala, M. M. Alam, and S. R. Adapa, Synlett 2004, 40, 3821 (d) A. S. Paraskar, G. K Dewkar, A. Sudalai, Tetrahedron Letters, 2003, 44, 3305. (e) Y. Ma, C. Qian, M. Wang, The Journal of organic chemistry, 2000, 65, 3864. (f) B. Ranu, A. Hajra, U. Jana, The Journal of organic chemistry, 2000, 65, 6270.
[10] (a) N. Li, X. H. Chen, J. Song Journal of the American Chemical Society 2009, 131, 15310. (b) X. H. Chen, X. Y. Xu, H. Liu, L. F. Cun, and L. Z. Gong, Journal of the American Chemical Society 2006, 128, 14802.
[11] R. S. Bhosale, S. V. Bhosale, T. Wang, P. K. Zubaidha, Tetrahedron Letters, 2004, 45, 9111.
[12] W.Y. Chen, S. Qin, J. R. Jin, catalysis communications 2007, 8, 123.
[13] (a) P. Shanmugam, G. Annie, and P. T. Perumal, Journal of Heterocyclic Chemistry 2003, 40, 879. (b). J. T. Li, J. F. Han, J. H. Yang, and T. S. Li, Ultrasonics Sonochemistry 2003, 10, 119.
[14] (a) P. Wipf and A. Cunningham, Tetrahedron Letters 1995, 36, 7819. (b) A. Dondoni and A. Massi, Tetrahedron Letters 2001, 42, 7975. (c) A. K. Bose, S. Pednekar, S. N. Ganguly, G. Chakraborty, and M. S. Manhas, Tetrahedron Letters 2004, 45, 8351.
[15] K. K. Pasunooti, H. Chai, C.N. Jensen, Tetrahedron Letters 2011, 52, 80.
[16] (a) J. J. Peng and Y. Q Deng, Tetrahedron Letters, 2001, 42, 5917. (b) J. C. Legeay, J. J. V. Eynde, and J. P. Bazureau, Tetrahedron Letters 2007, 48,1063. (c) B. Desai, D. Dallinger, and C. O. Kappe, Tetrahedron 2006, 62, 4651.
[17] (a) V. I. Parvulescu, C. Hardacre, Chemical Reviews, 2007, 107, 2615. (b) M. J. Earle, S. P. Katdare, K. R. Seddon, Organic Letters 2004, 6, 707.
[18] (a) B.C. Ranu, S. Banerjee, The Journal of organic chemistry 2005, 7, 3049. (b) B.C. Ranu, L. Adak, S. Banerjee, Canadian Journal of Chemistry 2007, 85, 366. (c) D. Saha, A. Saha, B.C. Ranu, Tetrahedron Letters 2009, 50, 6088.
[19] (a) A. Zare, A. R. Moosavi-Zare, A. Hasaninejad , Synthetic Communications 2009, 39, 3156. (b) A. Zare, A. R. Moosavi-Zare, A. Hasaninejad, Canadian Journal of Chemistry 2009, 87, 416. (c) A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri Rad, Journal of Combinatorial Chemistry 2010, 12,. 844.
[20] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Applied Catalysis A: General, 2011, 400, 70.
[21] R.J. Kalbasi, A. R.Massah, B.Daneshvarnejad, Applied Clay Science 2012, 55, 1.
[22] A. R. Hajipour, M. Seddighi, Synthetic Communications 2012, 42, 227.
[23] A. S. Paraskar, G. K. Dewkar, and A. Sudalai, Tetrahedron Letters 2003, 44, 3305.
[24] J. C. Rodrıguez-Domınguez, D. Bernardi, G. Kirsch, Tetrahedron Letters 2007, 48, 5777.
[25] Y. Ma, C. Qian, L. Wang, and M. Yang, “The Journal of organic chemistry, 2000, 65, 3864.
[26] M. M. Heravi, F. Derikvand, and F. F. Bamoharram, Journal of Molecular Catalysis A: Chemical 2005, 242, 3864.
[27] A.R. Hajipour, L. Khazdooz, A .Zarei, Synthetic Communications 2011, 41, 2200.
[28] E.Ramu, V.Kotra, N. Bansal, R. Varala, S.R. Adapa, Rasayan journal of chemistry 2008, 1, 188.
[29] K.A. Kumar, M. Kasthuraiah, C.S. Reddy, C. D. Reddy, Tetrahedron Letters 2001, 42,7873.
[30] M. Litvic, I. Vecenaj, Z. M. Ladisic , Tetrahedron 2010, 66, 3463.
[31] V.P. Garima, L. D. Srivastava, S. Yadav, Tetrahedron Letters 2010, 51, 6436.
[32] A. Debache, M. Amimour, A. Belfaitah, S. Rhouati,and B.Carboni, Tetrahedron Letters 2008, 49, 6119.
[33] K. K. Pasunooti, H. Chia, C. N. Jensen, Tetrahedron Letters 2011, 52, 80.
[34] A.Kumar, R. A. Maurya, Tetrahedron Letters 2007, 48, 4569.
[35] S. Tu, F. Fang, S. Zhu, Synlett, 2004, 3, 537.
[36] Y. Yu, D. Liu, C. Liu, G. Luo, Bioorganic & Medicinal Chemistry Letters 2007, 17, 3508.
[37] A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Letters 2003, 44, 4569.
[38] P. Salehi, M. Dabiri, M. A. Zolfigol, M. A. Bodaghi, Tetrahedron Letters 2003, 44, 2889.
[39] K. Vijay, S.Ganapaty, A.S. Rao, Asian Journal of Chemistry, 2010, 22, 2518.
[40] H. Adibi, H. A. Samimi, M. Beygzadeh, Catalysis Communications 2007, 8, 2119.
[41] M. Nasr-Esfahani, J. Hoseini, F. Mohammadi, Chinese Journal of Catalysis 2011, 32, 1484.
