Document Type : Original Research Article

Authors

1 Islami Azad University, Babol-Branch

2 Department of Chemistry, Faculty of Science, University of Kurdistan, Zip Code 66177-15175, Sanandaj, Iran

Abstract

N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was investigated as an efficient and magnetically recoverable catalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with variety aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be readily recovered easily by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. The advantages of this protocol are the use of a commercially available, eco-friendly, cheap, the mild reaction conditions, operational simplicity, practicability, short reaction times, and good to high yields

Graphical Abstract

Magnetic nanoparticle immobilized N-propylsulfamic acid: The efficient, green and reusable nanocatalyst for the synthesis of substituted coumarins

Keywords

Main Subjects

[1] C.O. Dalaigh, S.A. Corr, Y.K. Gun'ko, S.J. Connon, Angew. Chem. Int. Ed., 2007, 46, 4329-4332.
[2] F. Shi, M.K. Tse, M.-M. Pohl, A. Brückner, S. Zhang, M. Beller, Angew. Chem. Int. Ed., 2007, 46, 8866-8868.
[3] D. H. Zhang, G.D. Li, J.X. Li, J.S. Chen, Chem. Commun., 2008, 3414-3416. 
[4] S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L.V. Elst, Chem. Rev., 2008, 108, 2064-2110.
[5] C. T. Yavuz, J. T. Mayo, W.W. Yu, A. Prakash, J.C. Falkner, S. Yean, L.L. Cong, H. J. Shipley, A. Kan, M. Tomson, D. Natelson, V.L. Colvin, Science, 2006, 314, 964-967.
[6] B. Karimi, E.A Farhangi, Chem. Eur. J. 2011, 17, 6056-6060.
[7] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev., 2011, 111, 3036-3075.
[8] S. Rajasekaran, G.K. Rao, S.P.N. Pai, A. Ranjan, Int. J. Chem. Tech. Res., 2011, 3(2), 555-559.
[9] M.M. Heravi, B.H. Baghernejad, A. Oskooie, Curr. Org. Chem., 2009, 13, 1002-1014.
[10] M.M., Heravi, H., Alinejhad, K., Bakhtiari, H.A. Oskooie, Mol. Divers., 2010, 14, 621-626.
[11] P.O. Patil, S.B. Bari, S.D. Firke, P.K. Deshmukh, S.T. Donda, D.A.A. Patil, Bioorg. Med. Chem., 2013, 21, 2434-2450.
[12] M.A. Musa, J.S. Cooperwood, M.O.F. Khan, Curr. Med. Chem., 2008, 15, 2664-2679.
[13] M. Beinema, J.R. Brouwers, T. Schalekamp, B. Wilffert, Thromb. Haemost., 2008, 100, 1052-1057.
[14] S. Khodabakhshi, B. Karami, Tetrahedron Lett., 2014, 55, 7136-7139.
[15] Y. Shi, C.-H. Zhou, Bioorg. Med. Chem. Lett., 2011, 21, 956-960.
[16] S. Khodabakhshi, B. Karami, K. Eskandari, S.J. Hoseini, A. Rashidi, RSC Adv., 2014, 4, 17891-17895.
[17] S. Khodabakhshi, F. Marahel, A. Rashidi, M. Khaleghi-Abasabadi, J. Chin, Chem. Soc., 2015, 62, published online. 
[18] H. Ghasemnejad-Bosra, M. Faraje, S. Habibzadeh, F. Ramzaniyan-Lehmali, J. Serb. Chem. Soc., 2010, 75, 299-305.
[19] D. Azarifar, H.  Ghasemnejad-Bosra, Synthesis, 2006, 1123-1126.
[20] H. Ghasemnejad-Bosra, M. Haghdadi, I. Gholampour-Azizi, Heterocycles, 2008, 75, 391-395.
 
[21] H. Ghasemnejad-Bosra, M. Haghdadi, O. Khanmohamadi, M. Gholipour, G. Asghari, J. Chin. Chem. Soc., 2008, 55, 464-467.
[22] H. Ghasemnejad-Bosra, M. Faraje, S. Habibzadeh, Helv. Chim. Acta 2009, 92, 575-578.
[23] S. Habibzadeh, H. Ghasemnejad-Bosra, M. Faraji, Helv. Chim. Acta 2011, 94, 429-432.
[24] S. Habibzadeh, H. Ghasemnejad-Bosra, J. Chin. Chem. Soc., 2012, 59, 193-198.
[25] M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A-Gen., 2011, 395, 28-33.
[26] M. Kidwai, V. Bansal, P. Mothsra, Sh. Saxena, R.K. Somvanshi, Sh. Dey, T.P. Singh, J. Mol. Catal. A: Chem., 2007, 268, 76-81.
[27] R. Karimian, F. Piri, A.A. Safari, S.J. Davarpanah, J. Nanostructure Chem., 2013, 3, 52-57.
[28] J. Zhou, G. Gong, L. An, X. Sun, F. Zhu, Chin. J. Org. Chem., 2009, 29, 1988-1991.