Polyvinylpolypyrrolidone supported chlorosulfonic acid: An efficient catalyst for the one-pot synthesis of hexahydroquinolines
الموضوعات : Iranian Journal of Catalysis
Mahshid Yosefzadeh
1
(Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.)
Masoud Mokhtary
2
(Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.)
الکلمات المفتاحية: Multicomponent reaction, Polyvinylpolypyrrolidone, Chlorosulfonic acid, Hexahydroquinolines,
ملخص المقالة :
ABSTRACT Polyvinylpolypyrrolidone supported chlorosulfonic acid ([PVPP-SO3H]+Cl-) was synthesized and evaluated as a recoverable catalyst for the one-pot synthesis of hexahydroquinolines by reaction of arylaldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione) or 1,3-cyclohexanedione, ethylacetoacetate and ammonium acetate in high to excellent yield in ethanol at 70 °C. The [PVPP-SO3H]+Cl- catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR) and thermal gravimetric analysis (TGA). The capacity of the reagent was determined by titration and found to be 12 mmol/g, which shows a high loading of H+ per gram of the catalyst. Moreover, the catalyst could be recycled several times without significant loss of its catalytic activity. Clean methodologies, easy work-up procedure, high yield and simple preparation of the catalyst are some advantages of this work.
[1] F. Bossert, H. Meyer, E. Wehinger, Angew. Chem. Int. Ed. 20 (1981) 762-769.
[2] B. Sushilkumar, S. Devanand, Acta Pharm. (Zagreb, Croatia) 52 (2002) 281-287.
[3] R. Boer, V. Gekeler, Drugs Future 20 (1995) 499-509.
[4] G.A. Wachter, M.C. Davis, J. Med. Chem. 41 (1998) 2436-2438.
[5] S. Gullapalli, P. Ramarao, Neuropharmacology 42 (2002) 467-475.
[6] C.E. Sunkel, M. De casa Juana, L. Santos, J. Med. Chem. 33 (1990) 3205-3210.
[7] R. Shan, C. Velazquez, E. Knaus, J. Med. Chem. 47 (2004) 254-261.
[8] V. Klusa, Drugs Future 20 (1995) 135-138.
[9] R.G. Retzel, C.C. Bollen, E. Maeser, K.F. Drugs Future 17 (1992) 465-468.
[10] A. Hantzsch, Chem. Ber. 14 (1881) 1637-1638.
[11] L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z.Y. Fan, H. Tian, C.T. Qian, Tetrahedron 61 (2005) 1539-1543.
[12] S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loa, Synlett (2004) 831-835.
[13] J.L. Donelson, A. Gibbs, S.K. De, J. Mol. Catal. A: Chem. 256 (2006) 309-311.
[14] H. Adibi, H.A. Samimi, M. Beygzadeh, Catal. Commun. 8 (2007) 2119. 2119-2124.
[15] M.M. Heravi, K. Bakhtiri, N.M. Javadi, F.F. Bamoharram, M. Saeedi, H.A. Oskooi, J. Mol. Catal. A: Chem. 264 (2007) 50-52.
[16] A. Kumar, R.A. Maurya, Tetrahedron Lett. 48 (2007) 3887-3890.
[17] N.N. Karade, V.H. Budhewara, S.V. Shindeb, W.N. Jadhav, Lett. Org. Chem. 4 (2007) 16-19.
[18] C.S. Reddy, M. Raghu, Chin. Chem. Lett. 19 (2008) 775-779.
[19] M. Hong, C. Cai, W.B. Yi, J. Fluorine Chem. 131 (2010) 111-114.
[20] S.J. Song, Z.X. Shan, Y. Jin, Synth. Commun. 40 (2010) 3067-3077.
[21] M. Saha, A.K. Pal, Tetrahedron Lett. 52 (2011) 4872-4877.
[22] S. Sheik Mansoor, K. Aswin, K. Logaiya, S.P.N. Sudhan, J. Saudi Chem. Soc. (2012) in press, doi: 10.1016/j.jscs. 2012.09.010.
[23] R. Surasani, D. Kalita, A.V. Dhanunjaya Rao, K. Yarbagi, K.B. Chandrasekhar, J. Fluorine Chem. 135 (2012) 91-96.
[24] M. Tajbakhsh, E. Alaee, H. Alinezhad, M. Khandan, F. Jahani, S. Khaksar, P. Rezaee, M. Tajbakhsh, Chin. J. Catal. 33 (2012) 1517-1522.
[25] A. Khazaei, M.A. Zolfigol, A.R. Moosavi‐Zare, J. Afsar, A. Zare, V. Khakyzadeh, M.H. Beyzavi, Chin. J. Catal. 34 (2013) 1936-1944.
[26] B. Maleki, R. Tayebee, M. Kermanian, S.S. Ashrafi, J. Mex. Chem. Soc. 57 (2013) 290-297.
[27] A. Zare, F. Abi, A.R. Mossavi-Zare, M.H. Beyzavi, M.A. Zolfigol, J. Mol. Liq. 178 (2013) 113-121.
[28] M. Ghorbani, H.R. Shaterian, S. Noura, F. Khammar, K. Behbodi, B. Reisi, M. Oftadeh, J. Mol. Liq. 204 (2015) 15-20.
[29] M. Nasr-Sefahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, H. Nasrabi, J. Mol. Catal. A: Chem. 382 (2014) 99-105.
[30] S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, S.J. Taylor, J. Chem. Soc. Perkin. Trans 1 (2000) 3815-4195.
[31] M. Mokhtary, M.M. Lakouraj, Chin. Chem. Lett. 22 (2011) 13-17.
[32] M. Mokhtary, F. Najafizadeh, C. R. Chim. 15 (2012) 530-532.
[33] M. Mokhtary, S. Refahati, Dyes Pigm. 99 (2013) 378-381.
[34] M. Mokhtary, S.A. Mirfarjood Langroudi, Monatsh Chem. 145 (2014) 1489-1494.
[35] S. Sahoo, P. Kumar, F. Lefebvre, S.B. Halligudi, Appl. Catal. A 354 (2009)17-25.
[36] L.L. Zhu, Y.H. Liu, J. Chen, Ind. Eng. Chem. Res. 48 (2009) 3261-3267.
[37] V. Bühler, Polyvinylpyrrolidone Excipients for Pharmaceuticals: Povidone, Crospovidone and Copovidone, Berlin, Heidelberg, New York: Springer. (2005) 1–254.
[38] S. Ganesan, J. Felo, M. Saldana, V.F. Kalasinsky, M. R. Lewin-Smith, J.F. Tomashefski Jr, Mod. Pathol. 16 (2003) 286–292.
