Nano-Silica phosphoric acid: an efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (thiones) under solvent-free or sonication conditions

Authors

1 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R.Iran.

2 Department of Chemistry, College of Science, Yazd University, I. R. Iran .

Abstract

Two simple protocols for the synthesis of three-component condensation reaction of an aldehyde, β-ketoester and urea or thiourea to obtain the 3, 4-dihydropyrimidin-2(1H)-ones (thiones) using nano silica phosphoric acid are reported. Short reaction times, high yields, reusability of catalyst and easy workup are some advantages of these protocols.

Keywords


[1] (a) H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Takeuchi, M. Hamaguchi, K. Aisaka, T. Hidaka, M. Kawai, M. Takeda,T. Ishihara, K. Funahashi, F. Satoh, M. Morita, T. Noguchi, J. Med. Chem. 32 (1989) 2399-2406 (b) K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A.O. Hedberg, B.C. Reilly, J. Med. Chem. 34 (1991) 806-811.

[2] M.M. Amini, A. Shaabani, A. Bazgir, Catal. Commun. 7 (2006) 843–847.

[3] M.M. Heravi, F. Derikvand, F. Bamoharram, J. Mol. Catal. A: Chem. 242 (2005) 173-175.

[4] Y. Yu, D. Liu, C. Liu, G. Luo, Bioorg. Med. Chem. Lett. 17 (2007) 3508-3510.

[5] H.R. Kalita, P. Phukan, Catal. Commun. 8 (2007) 179–182.

[6] H. Adibi, H.A. Samimi, M. Beygzadeh, Catal. Commun. 8 (2007) 2119–2124.

[7] S. Chitra, K. Pandiarajan, Tetrahedron Lett. 50 (2009) 2222–2224.

[8] M.A. Bigdeli, S. Jafari, G.H. Mahdavinia, H. Hazarkhani, Catal. Commun. 8 (2007) 1641–1644.

[9] C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu, V.V.N. Reddy, Tetrahedron Lett. 43 (2002) 2657–2659.

[10] J.T. Li, J.F. Han, J.H. Yang, T.S. Li, Ultrasonics Sonochem. 10 (2003) 119 –122.

[11] N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor, B.M. Bhanage, J. Mol. Catal. A: Chem. 271 (2007) 14-17.

[12] B.F. Mirjalili, A. Bamoniri, A. Akbari J. Iran. Chem. Soc. 8 (2011)135-140.

[13] M.A. Zolfigol, F. Shirini, K. Zamani, E. Ghofrani, S. Ebrahimi, Phosphourus, Sulfur, Silicon Relat. Elem.179 (2004) 2177-2182.

[14] M.A. Zolfigol, F. Shirini, A. Ghorbani Choghamarani, A. Shiri, H. Keypour, S. Salehzadeh Asian, J. Chem. 13 (2001) 849-853.

[15] A. Bamoniri, M.A. Zolfigol, I. Mohammadpoor-Baltork, B.F. Mirjalili, J. Iran. Chem. Soc. 3 (2006) 85-88.

[16] A. Bamoniri, B.F. Mirjalili, M.A. Zolfigol, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 4 (2007) 332-335.

[17] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc. 8 (2011) 129-134.

[18] B. Sadeghi, B.F. Mirjalili, M.M. Hashemi, J. Iran. Chem. Soc. 5 (2008) 694-698.

[19] A. Bamoniri, B.F. Mirjalili, A. Ghorbani-Ch., M. E. Yazdanshenas, A. Shayanfar, A. Akbari, Iran. J. Catal. 2 (2011) 51-54.

[20] B.F. Mirjalili, A. Bamoniri, A. Akbari, Iran. J. Catal. 2 (2011) 87-92.

[21] F.L. Zumpe, M.B. Flu, K. Schmitz, A. Lender, Tetrahedron Lett. 48 (2007) 1421-1423.

[22] M. M. Heravi, K. Bakhtiari, F.F. Bamoharram, Catal. Commun. 7 (2006) 373-376.

[23] J.C. Rodrıguez-Domınguez, D. Bernardi, G. Kirsch, Tetrahedron Lett. 48 (2007) 5777-5780.

[24] B. Liang, X. Wang, J-X Wang, Z. Du, Tetrahedron 63 (2007) 1981–1986.

[25] P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Tetrahedron Lett. 44 (2003) 2889–2891.