Phospho sulfonic acid: an efficient solid acid catalyst for the facile preparation of 1,4-dihydropyridines

Document Type: Articles

Authors

Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, I. R. Iran

Abstract

A simple and mild one-pot three-component reaction for the preparation 1,4-dihydropyridines has been developed from various aldehyde substrates, 1,3-dicarbonyl compounds (dimedone) and ammonium acetate (Hantzsch method) in the presence of a catalytic amount of phospho sulfonic acid (PSA) as an efficient and heterogeneous solid acid in EtOH at room temperature. Preparation of PSA is straightforward and handling of the reagent is also easy. The attractive features of this protocol are: (i) The elimination of corrosive liquid acids; (ii) the use of an inexpensive and relatively non-toxic catalyst, and (iii) reusability of the catalyst.

Keywords


[1] E. Kolvari, N. Koukabi, M.M. Hosseini, J. Mol. Catal. A: Chem. 397 (2015)68-75.
[2] M. Hosseini-Sarvari, Z. Razmi, Appl. Surf. Sci. 324 (2015) 265-274.
[3] K. Wilson, J.H. Clark, Pure Appl. Chem. 72 (2000) 1313-1319.
[4] A. Davoodnia, A. Tavakoli-Nishaburi, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32 (2011) 635-638.
[5] P. Slobbe, E. Ruijter, R.V.A. Orru, Med. Chem. Commun. 3 (2012) 1189-1218.
[6] A. Dömling, I. Ugi. Chem. Intl. Ed. 39 (2000) 3168-3210.
[7] S. Pednekar, R. Bhalerao, N. Ghadge, J. Chem. Sci. 125 (2013) 615–621.
[8] M. Suarez, Y. Verdecia, B. Illescas, R. Martinez-Alvarez, A. Avarez, E. Ochoa, C. Seoane, N. Kayali, N. Martin, Tetrahedron 59 (2003) 9179-9186.
[9] A. Zarghi, H. Sadeghi, A. Fassihi, F.M. Aizi, A. Shafiee, Il Farmaco. 58 (2003) 1077-1081.
[10] M.E. Ortiz, L.J. Nunez-Vergara, J.A. Sequella, Pharm. Res. 20 (2003) 292-296.
[11] R. Budriesi, A. Bisi, P. Ioan, A. Rampa, S. Gobbi, F. Belluti, L. Piazzi, P. Valenti, A. Chiarini, Bioorg. Med. Chem. 13 (2005) 3423-3430.
[12] R. Miri, K. Javidnia, H. Sarkarzadeh, B. Hemmateenejad, Bioog. Med. Chem. 14 (2006) 4842-4849.
[13] A. Heydari, S. Khaksar, M. Tajbakhsh, H.R. Bijanzadeh, J. Fluorine Chem. 130 (2009) 609-614.
[14] S. Ko, M.N.V. Sastry, C. Lin, C.F. Yao, Tetrahedron Lett. 46 (2005) 5771-5774.
[15] G. Sabitha, G.S.K.K. Reddy, C.H.S Reddy, J.S. Yadav, Tetrahedron Lett. 44 (2003) 4129-4113.
[16] G.V.M. Sharma, K.L. Reddy, P.S. Lakshmi, P.R. Krishna, Synthesis 1 (2006) 55-58.
[17] G. Sabitha, K. Arundhathi, K. Sudhakar, B.S. Sastry, J.S. Yadav, Synth. Commun. 39 (2009) 2843-2851.
[18] J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A: Chem. 256 (2006) 309-311.
[19] A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50 (2009) 5248-5250.
[20] G. Sabitha, G.S.K. Kumar Reddy, Ch.Srinivas Reddy, J.S. Yadav, Tetrahedron Lett. 44(2003) 4129–4131.
[21] A.R Kiasat, A. Mouradzadegun, S.J. Saghanezhad, J. Serb. Chem. Soc. 78 (2013) 469–476.
[22] S. Sajjadifar, S. Rezayati, Chem. Pap. 68 (2014) 531-539.
[23] A.R. Kiasat, M. Fallah-Mehrjardi, J. Braz. Chem. Soc. 19 (2008) 1595-1599.
[24] R. Hajinasiri, S. Rezayati, Z. Naturforsch. 68B (2013) 818–822.
[25] D. Zareyee, M. Serehneh, J. Mol. Catal. A: Chem. 391 (2014) 88–91.
[26] D. Zareyee, P. Alizadeh, M.S. Ghandali, M.A. Khalilzadeh, Chem. Pap. 67 (2013) 713-721.
[27] M. Dabiri, S.C. Azimi, A. Bazgir, Chem. Pap. 62 (2008) 522–526.
[28] B. Karimi, D. Zareyee, Org. Lett. 10 (2008) 3989-3992.
[29] A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, H. Goudarziafshar, M. Nikoorazm, S. Yousefi, B. Tahmasbi, J. Braz. Chem. Soc. 22 (2011) 525-531.
[30] M. Anniyappam, D. Muralidharan, P.T. Perumal, Synth. Commun. 32 (2002) 659–663.
[31] J.S. Yadav, B.V. Subba Reddy, P. Thirupati, Synth. Commun. 31 (2001) 425–430.
[32] A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Synlett 4 (2008) 509–512.
[33] F. Tamaddon, Z. Razmi, A.A. Jafari, Tetrahedron Lett. 51 (2010) 1187–1189.
[34] A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50 (2009) 5248–5250.
[35] J.J.V. Eynde, F. Delfosse, A. Mayence, Y.V. Haverbeke, Tetrahedron 51 (1995) 6511-6516.
[36] N.N. Karade, V.H. Budhewara, S.V. Shindeb, W.N. Jadhav, Lett. Org. Chem. 4 (2007) 16-19.
[37] J.P. Nirmal, P.V. Dadhaniya, M.P. Patel, R.G. Patel, Indian J. Chem. 49 (2010) 587-592.
[38] E. Kolvari, M.A. Zolfigol, N. Koukabi, B. Shirmardi-shaghasemi, Chem. Pap. 65 (2011) 898-902.
[39] D. Bandyopadhyay, S. Maldonado, B.K. Banik, Molecules 17 (2012) 2643-2662.
[40] F. Farzaneh, E. Zamanifar, L.J. Foruzin, M. Ghandi, J. Sci. I. R. Iran. 23 (2012) 313-318.
[41] M. Arslan, C. Faydali, M. Zengin, M. Kucuk, H. Demirhan, Turk. J. Chem. 33 (2009) 769-774.
[42] B. Palakshi Reddy, K. Rajesh, V. Vijayakumar. J. Chin. Chem. Soc. 58 (2011) 384-388.