Melamine trisulfonic acid as an efficient and reusable catalyst for the crossed-Aldol condensation of ketones and aldehydes under solvent-free conditions

Authors

Department of Chemistry, College of Science, University of Guilan, Rasht, I.R. Iran.

Abstract

Various types of aldehydes undergo crossed-Aldol condensation with ketones in the presence of melamine trisulfonic acid (MTSA) under solvent-free conditions. The reported method is mild, efficient and has the advantages such as using heterogeneous catalysis, short reaction times, high yields of the products and the recyclability of the catalyst.

Keywords


[1] J. Deli, T. Lorand, D. Szabo, A. Foldesi, Pharmazie 34 (1984) 539-540.
[2] M. Ogawa, Y. Ishii, T. Nakano, S. Irifune, 1988 JP 63192446, [Chem. Abstr. 1988, 63, 238034]. 
[3] J. Kawamata, K. Inoue, T. Inabe, M. Kiguchi, M. Kato, Y. Taniguchi, Chem. Phys. Lett. 249 (1996) 29-34. 
[4] J.R.A. Dimmock, M.P. Padmanilayam, G.A. Zello, K.H. Nienaber, T.M. Allen, C.L. Santos, E. De Clercq, J. Balzarini, E.K. Manavathu, J.P. Stables, Eur. J. Med. Chem. 38 (2003) 169-177.
[5] K. Gangadhara, K. Kaushal, Polymer 36 (1995) 1903-1910.
[6] A.T. Nielsen, W. Houlihan, J. Org. React. 16 (1968)
1-10.
[7] K. Irie. K. Watanabe, Bull. Chem. Soc. Jpn. 53 (1980) 1366-1371.
[8] M. Zheng, L. Wang, J. Shao, Q. Zhong, Synth. Commun. 27 (1997) 351-354. 
[9] N. Iranpoor, F. Kazemi, Tetrahedron 54 (1998) 9475-9480.
[10] W. L.Bao, Y.M. Zhang, Chin. J. Org. Chem. 18 (1998) 272-242. 
[11] T. Nakano, T. Migita, Chem. Lett. (1993) 2157-2158.
[12] N. Iranpoor, B. Zeynizadeh, A. Aghapour, J. Chem. Res. (S) (1999) 554-555.
[13] J.T. Li, W.Z. Yang, G.F. Chen, T.S. Li, Synth. Commun. 33 (2003) 2619-2625.
[14] J.S. Yadav, B.V. Subba Reddy, A. Nagaraju, J.A.R.P. Sarma, Synth. Commun. 32 (2002) 893-896.
[15] X.Y. Zhang, X.S. Fan, H.Y. Niu, J.J. Wang, Green Chem. 5 (2003) 267-269.
[16] D.F. Huang, J.X. Wang, Y.L. Hu, Chin. Chem. Lett. 14 (2003) 333-334.
[17] L. Yang, J. Lu, Y.J. Bai, Chin. J. Org. Chem.23 ( 2003) 659-661.
[18] G. Deng, T. Ren, Synth. Commun. 33 (2003) 2995-3001.
[19] M. S. Abaee, M.M. Mojtahedi, R. Sharifi, M.M. Zahedi, H. Abbasi, K. Tabar-Heidar, J. Iran. Chem. Soc. 3 (2006) 293-296.
[20] P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, J. Braz. Chem. Soc. 15 (2004) 773-776.
[21] B. Das, P. Thirupathi, I. Mahender, K. Ravinder Reddy, J. Mol. Catal. A: Chem. 247 (2006) 182-185.
[22] L. Wang, J. Sheng, H. Tian, J. Han, Z. Fan, C. Qian, Synthesis (2004) 3060-3064.
[23] G. Mohammadi Ziarani, A. Badiei, A. Abbasi, Z. Farahani, Chin. J. Chem. 27 (2009) 1537-1542.
[24] L.T. An, J.P. Zou, L.L. Zhang, Catal. Commun. 9 (2008) 349-354.
[25] W.B. Yi, C. Cai, J. Fluorine Chem. 130 (2009) 484-487.
[26] A. Zali, K. Ghani, A. Shokrolahi, M.H. Keshavarz, Chin. J. Catal. 29 (2008) 602-606.
[27] P. Salehi, M.M. Khodaei, M.A. Zolfigol, A. Keyvan, Monatsh. Chem. 133 (2002) 1291-1295.
[28] S. Bhagat, R. Sharma, A.K. Chakraborti, J. Mol. Catal. A: Chem. 260 (2006) 235-240.
[29] F. Shirini, M.A. Zolfigol, J. Albadi, Synth. Commun. 40 (2010) 910-914.
[30] F. Shirini, M.A. Zolfigol, A.R. Aliakbar, J. Albadi, Synth. Commun, 40 (2010) 1022-1028.
[31] F. Shirini, M.A. Zolfigol, J. Albadi, Chin. Chem. Lett. 22 (2011) 318-321.
[32] F. Shirini, M.A. Zolfigol, J. Albadi, J. Iran. Chem. Soc. 7 (2010) 895-899.
[33] F. Shirini, J. Albadi, Bull. Korean Chem. Soc. 31 (2010) 1119-1120.
[34] W. Ma, X. Wang, F. Yan, L. Wu, Y. Wang, Monatsh. Chem. 142 (2011) 163-167.
[35] R.K. Behera, A. Nayak, Indian J. Chem. 14B (1976) 223-224.