Application of SBA-Pr-SO3H as a solid acid nanoreactor in the Biginelli reaction

Document Type: Articles

Authors

1 Department of Chemistry, Alzahra University, Vanak Square, P.O. Box 1993893973, Tehran, Iran.

2 School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran.

Abstract

Sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) with a pore size of 6 nm catalyzed three component coupling of aromatic aldehydes, urea and ethyl acetoacetate to afford the corresponding dihydropyrimidinones under solvent free condition. This new protocol for Biginelli reaction has important advantages such as green synthesis, short reaction time, easy isolation and high yields of products and reusability of the catalyst. SBA-Pr-SO3H was proved to be an efficient heterogeneous nanoporous solid acid catalyst which could be easily handled and removed from the reaction mixture by simple filtration and can be recovered and reused for several times without any loss of activity.

Keywords


[1] S.L. Jain, J.K. Joseph, S. Singhal, B. Sain, J. Mol. Catal. A: Chem. 268 (2007) 134-138.
[2] C. Oliver Kappe, Tetrahedron 49 (1993) 6937-6963.
[3] J.P. Wan, Y. Pan, Mini-Rev. Med. Chem. 12 (2012) 337-349.
[4] İ.S. Zorkun, S. Saraç, S. Çelebi, K. Erol, Bioorg. Med. Chem. 14 (2006) 8582-8589.
[5] K.B. Goodman, H. Cui, S.E. Dowdell, D.E. Gaitanopoulos, R.L. Ivy, C.A. Sehon, R.A. Stavenger, G.Z. Wang, A.Q. Viet, W. Xu, G. Ye, S.F. Semus, C. Evans, H.E. Fries, L.J. Jolivette, R.B. Kirkpatrick, E. Dul, S.S. Khandekar, T. Yi, D.K. Jung, L.L. Wright, G.K. Smith, D.J. Behm, R. Bentley, C.P. Doe, E. Hu, D. Lee, J. Med. Chem. 50 (2006) 6-9.
[6] C.O. Kappe, Acc. Chem. Res. 33 (2000) 879-888.
[7] C.Y. Hong, Y. Kishi, J. Am. Chem. Soc. 114 (1992) 7001-7006.
[8] M. Wiese, P.M. Dagostino, T.K. Mihali, M.C. Moffitt, B.A. Neilan, Mar. Drugs 8 (2010) 2185-2211.
[9] C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature 359 (1992) 710-712.
[10] J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins, J.L. Schlenker, J. Am. Chem. Soc. 114 (1992) 10834-10843.
[11] D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279 (1998) 548-552.
[12] K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal. Sci. Technol. 1 (2011) 389-393.
[13] P. Gholamzadeh, G.M. Ziarani, A. Badiei, Z. Bahrami, Eur. J. Chem. 3 (2012) 279-282.
[14] G. Mohammadi Ziarani, A. Abbasi, A. Badiei, Z. Aslani, E-J. Chem. 8 (2011) 293-299.
[15] G. Mohammadi Ziarani, A. Badiei, Y. Khaniania, M. Haddadpour, Iran. J. Chem. Chem. Eng. 29 (2010) 1-10.
[16] G. Mohammadi Ziarani, A.R. Badiei, M. Azizi, Sci. Iran. 18 (2011) 453-457.
[17] P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, A. Abolhassani Soorki, N. Lashgari, Res. Chem. Intermed. 39 (2013) 3925-3936.
[18] G. Mohammadi Ziarani, N. Lashgari, A.R. Badiei, Sci. Iran. 20 (2013) 580-586.
[19] G. Mohammadi Ziarani, A. Badiei, S. Mousavi, N. Lashgari, A. Shahbazi, Chin. J. Catal. 33 (2012) 1832-1839.
[20] G.M. Ziarani, A. Badiei, M. Azizi, N. Lashgari, J. Chin. Chem. Soc. 60 (2013) 499-502.
[21] M. Adib, K. Ghanbary, M. Mostofi, M. Ganjali, Molecules 11 (2006) 649-654.
[22] F.S. Falsone, C.O. Kappe, Arkivoc 2 (2001) 122-134.
[23] M. Li, W.-S. Guo, L.-R. Wen, Y.-F. Li, H.-Z. Yang, J. Mol. Catal. A: Chem. 258 (2006) 133-138.
[24] J.K. Joseph, S.L. Jain, B. Sain, J. Mol. Catal. A: Chem. 247 (2006) 99-102.
[25] M.A. Bigdeli, S. Jafari, G.H. Mahdavinia, H. Hazarkhani, Catal. Commun. 8 (2007) 1641-1644.
[26] Ş. Beşoluk, M. Küçükislaoğlu, M. Zenğin, M. Arslan, M. Nebioğlu, Turk. J. Chem. 34 (2010) 411-416.
[27] W. Su, J. Li, Z. Zheng, Y. Shen, Tetrahedron Lett. 46 (2005) 6037-6040.
[28] R. Tayebee, M.M. Amini, M. Ghadamgahi, M. Armaghan, J. Mol. Catal. A: Chem. 366 (2013) 266-274.
[29] J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 41 (2012) 6173-6181.
[30] H. Murata, H. Ishitani, M. Iwamoto, Org. Biomol. Chem. 8 (2010) 1202-1211.
[31] T. Boumoud, B. Boumoud, S. Rhouati, A. Belfaitah, A. Deache, P. Mosset, Acta Chim. Slov. 55 (2008) 617-622.
[32] M. Maheswara, S.H. Oh, K. Kim, J.Y. Do, Bull. Korean Chem. Soc. 29 (2008) 1752-1754.
[33] I. Cepanec, M. Litvić, M. Filipan-Litvić, I. Grüngold, Tetrahedron 63 (2007) 11822-11827.
[34] D. Angeles-Beltrán, L. Lomas-Romero, V. Lara-Corona, E. González-Zamora, G. Negrón-Silva, Molecules 11 (2006) 731-738.
[35] Y. Yu, D. Liu, C. Liu, G. Luo, Bioorg. Med. Chem. Lett. 17 (2007) 3508-3510.
[36] G. Sabitha, G.S.K. Kumar Reddy, C.S. Reddy, J.S. Yadav, Synlett (2003) 0858-0860.
[37] N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, C. Peppe, Tetrahedron 58 (2002) 4801-4807.
[38] K.K. Pasunooti, H. Chai, C.N. Jensen, B.K. Gorityala, S. Wang, X.-W. Liu, Tetrahedron Lett. 52 (2011) 80-84.
[39] H. Khabazzadeh, K. Saidi, H. Sheibani, Bioorg. Med. Chem. Lett. 18 (2008) 278-280.
[40] J.S. Yadav, B.V.S. Reddy, E.J. Reddy, T. Ramalingam, J. Chem. Res. 2000 (2000) 354-355.