Comparison of Catalytic Effect of Alkali and Alkaline Earth Metals Hydrogen Sulfate: As the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

Document Type: Research Article

Authors

Department of Chemistry, Shahid Beheshti University, P. O. Box 19396-4716, Tehran, I.R. IRAN

Abstract

Alkali and alkaline earth metals hydrogen sulfate catalyzed the one-pot three component condensation reactions of aldehydes, 1,3-dicarbonyl compounds and urea or thiourea under solvent-free conditions leading to 3,4-dihydropyrimidin-2(1H)-ones in high yields at 80 °C. Our results showed that Biginelli reaction not only is pH dependent, but the cation of catalyst plays an important role. 

Keywords

Main Subjects


[1] Biginelli, P., Gazz. Chim. Ital.,  23, 360 (1893).
[2] Kappe, C.O., Tetrahedron,  49, 6937 (1993).
[3] (a)Atwal, K.S., Swanson, B.N., Unger, S.E., Floyd, D.M., Moreland, S., Hedberg,  A., O’Reilly, B.C., J. Med. Chem., 34,806 (1991). (b) Rovnyak, G.C., Kimball, S.D., Beyer, B., Cucinotta, G., DiMarco, J.D., Gougoutas, J.Z., Hedberg, A., Malley, M.F., McCarthy, J.P., Zhang, R., Moreland, S., J. Med. Chem., 38, 119 (1995).
[4] Kumar, K.A., Kasthuraiah, M., Reddy, C.S., Reddy, C.D., Tetrahedron Lett., 42, 7873 (2001).
[5] Ranu, B.C., Hajra, A., Jana, U., J. Org. Chem., 65, 6270 (2000).
[6] Reddy, Ch.V., Mahesh, M., Raju, P.V.K., Babu, T.R., Reddy, V.N., Tetrahedron  Lett., 43, 2657 (2002).
[7] Yadav, J.S., Reddy, B.V.S., Srinivas, R.,  Venugopal, C., Ramalingam, T., Synthesis, 1341 (2001).
[8] Paraskar,  A. S.,  Dewkar, G.  K., Sudalai, A., Tetra-hedron Lett., 44, 3305 (2003).
[9] Fu, N.Y., Yuan, Y.F., Cao, Z., Wang, S.W., Tetra-hedron, 58, 4801 (2002).
[10] Tu, S., Fang, F., Zhu, S., Li, T., Zhang, X., Zhuang, Q., Synlett, 537 (2004).
[11] Xia, M.,  Wang, Y. G.,  Tetrahedron  Lett., 43, 7703 (2002).
[12] Bose, D. S., Fatima, L., Mereyala, H. B., J. Org.  Chem., 68, 587 (2003).
[13] Dondoni, A.,Massi, A., Tetrahedron  Lett., 42, 7975 (2001).
[14] Ma, Y., Qian, C., Wang, L., Yang, M., J.Org. Chem., 65, 3864 (2000).
[15] Shaabani, A., Bazgir, A., Teimouri, F., Tetrahedron Lett.,44, 857 (2003).
[16] Peng, J., Deng, Y., Tetrahedron Lett.,42, 5917 (2001).
[17] Bigi, F., Carloni, S., Frullanti, B., Maggi, R., Sartori, G., Tetrahedron Lett., 40, 3465 (1999).
[18] Yadav, J. S., Reddy, B. V. S., Reddy, E. J., Rama-lingam, T., J. Chem. Research(S), 354 (2000).
[19] Kappe, C.O., Kumar, D., Varma, R.S., Synthesis, 1799 (1999).
[20] Stadler, A., Kappe, C.O., J. Chem. Soc. Perkin Trans., 2, 1363 (2000).
[21] Stefani,  H. A.,  Gatti, P. M., Synth.  Commun.,  30, 2165 (2000).
[22] Yadav, J.S., Reddy, B.V.S., Reddy, K.B., Raj, K.S., Prasad, A.R., J. Chem. Soc. Perkin Trans. 1, 1939 (2001).
[23] Li, J.T., Han, J. F., Yang, J., Li, T. S., Ultrason. Sonochem., 10, 119 (2003).
[24] Shaabani, A., Bazgir, A., Bijanzade, H.R., Mol. Div., 8, 141 (2004).
[25] Shaabani, A., Bazgir, A., Tetrahedron Lett., 45, 2575 (2004).
[26] Pearson, R.G., Inorg. Chem., 27, 734 (1988).
[27] Eynde, J.J.V., Audiart, N., Canonne, V., Michel, S., Haverbeke, Y.V., Kappe, C.O., Heterocycles, 45, 1967 (1997).
[28] Hu, E.H., Sidler, D.R., Dolling, U.H., J. Org. Chem., 63, 3454 (1998).
[29] Lu,  J., Bai, Y., Wang, Z., Yang, B.,  Ma,  H., Tetra-hedron Lett., 41, 9075 (2000).