Nanoparticles Poly Ethylene Imine-Functionalized MCM- as a Solid Catalyst for Multi-Component Reactions

Document Type: Original Paper

Authors

1 Department of Chemistry, College of Science, ShahidChamran University, Ahvaz, Iran

2 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

Abstract

A novel magnetically immobilized polyethyleneimine (PEI)
fabricated by covalently anchoring on MCM-41 (MCM-41@PEI)
was prepared. The synthesized catalyst was characterized by Fourier
transform infrared (FT-IR), thermogravimetric analysis (TGA), X-ray
powder diffraction (XRD), scanning electron microscopy (SEM) and
transmission electron microscopy (TEM). The immobilized PEI was
shown to be an efficient heterogeneous catalyst for the synthesis of
spiro-oxindole and benzopyranes derivatives via multi-component
reaction (MCR), in ethylene glycol as a green solvent. No leaching
problem was observed after several runs, while the catalyst can be
recovered and reused without loss of reactivity under the described
reaction conditions.

Keywords


[1] N. T. S. Phan, C. S. Gill, J. V. Nguyen, Z. J. Zhang and C. W. Jones, Angew. Chem., Int.
Ed., 2006, 45, 2209–2212.
[2] S. Shylesh, V. Schunemann, W.R. Thiel, Angew. Chem. Int. Ed. 2010, 49, 3428.
[3] A. Kong, P. Wang, H. Zhang, F. Yang, S.P. Huang, Y. Shan, Appl. Catal. 2012, A 417,183.
[4] A. Baiker, Chem. Rev., 1998, 99, 453–474.
[5] H. Hamadi, M. kooti,
[6] C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature. 1992,359, 710–712.

[7] W. Zhang, T.R. Pauly, T.J. Pinnavaia, Chem. Mater. 1997, 9,2491–2498.
[8]E.P. Ng, S. Mintova, Micropor. Mesopor. Mater. 2008, 114,1–26.
[9] Beck J. S., Vartuli J. C., Roth W. J., Leonowicz M. E., Kresge C. T., Schmitt K. D., Chu C. T. W., Olson D. H., Sheppard E. W., McCullen S. B., Higgins J. B., Schlenker J. L., J. Am. Chem. Soc., 1992, 114, 10834—10843.
[10] Song C. E., Lee S. G., Chem. Rev., 2002, 102, 3495-3524.
[11] P. Selvam, S.E. Dapurkar, Catal. Today,2004, 96, 135–141.
[12] J.C. Juan, J. Zhang, M.A. Yarmo, J. Mol. Catal. A: Chem. 2007, 267,265–271.
[13] G. Karthikeyan, A. Pandurangan, J. Mol. Catal. A: Chem. 2009, 311,36–45.
[14] E.-P. Ng, H. Nur, K.-L. Wong, M.N.M. Muhid, H. Hamdan, Appl. Catal. A: Gen. 2007,323, 58–65.
[15] D.P. Sawant, A. Vinu, F. Lefebvre, S.B. Halligudi, J. Mol. Catal. A: Chem. 2007, 262,98–108.
[16] N.E. Poh, H. Nur, M.N.M. Muhid, H. Hamdan, Catal. Today. 2006, 114,257–262.
[17] A. Shaabani, M. Mohammadpour, S. Ghasemi, R. Ghadari, A. H. Rezayan, Y. Fazaeli, S. Feizi, Chem. Pharm. Bull. 2010, 58, 270—272.
[18] J.-P. Dacquin, H.E. Cross, D.R. Brown, T. Duren, J.J. Williams, A.F. Lee, K. Wilson, Green Chem. 2010, 12, 1383–1391.
[19] X. Sheng, J. Gao, L. Han, Y. Xia, W. Sheng, Micropor. Mesopor. Mater. 2011, 143, 73– 77.
[20] S. Shylesh, P.P. Samuel, C. Srilakshmi, R. Parischa, A.P. Singh, J. Mol. Catal. A: Chem. 2007, 274, 153–158.
[21] F. Adam, K.M. Hello, T.H. Ali, Appl. Catal. A: Gen.2011, 399, 42–49.
[22] B. Rac, P. Hegyes, P. Forgo, A. Molnar, Appl. Catal. A: Gen. 2006, 299,193–201.
[23] E-P. Ng, S. N. M. Subari, O. Marie, R. R. Mukti, J-C. Juan Appl. Catal. A: Gen. 2013, 450, 34– 41
[24] R.V. Hangarge, S.A. Siddiqui, S.R. Shengule, M.S. Shingare, Mendeleev Commun. 2002, 12, 209–210.
[25] K-Z. Hossain, C. M. Monreal, A. Sayari,Colloids and Surfaces B: Biointerfaces, 2008, 62, 42–50

[26] C. Rudolph, J. Lausier, S. Naundorf; RH. Müller, J. Rosenecker, J. Gene. Med.,2000, 4, 269.
[27] B. Chertok, A. E. David, V. C. Yang, Biomat. 2010, 31, 6317.
[28] A. Barnard, P. Posocco, S. Pricl, M. Calderon, R. Haag, M. E. Hwang, V. W. T. Shum, D. W. Pack, D. K. Smith, J. Amr. Chem. Soc, 2011, 133, 20288.
[29] S. Satyapal, T. Filburn, J. Trela, J. Strange, Energy & Fuels, 2001, 15, 250.
[30] J.J. Karimpil, J.S. Melo, S.F. D’Souza, Int. J. Biol. Macromol. 2012, 50, 300.
[31] C. T. Chen, L. Y. Wang, Y. P. Ho, Anal Bioanal Chem. 2011, 399, 2795.
[32] W-J. Song, J-Z. Du, T-M. Sun, P.-Z. Zhang, J. Wang, Small. 2010, 6, 239.
[33] H. J. Lee, S. G. Lee, E. J. Oh, H. Y. Chung, S. I. Han, E. J. Kim, S. Y. Seo, H. D. Ghim,J. H. Yeum, J. H. Choi, Coll. Surf B Biointerfaces. 2011, 88, 505.
[34] X. Wang, L. Zhou, Y. Ma, X. Li, H. Gu, Nano Res. 2009,2, 365.
[35] X. Wang, L. Zhou, Y. Ma, X. Li; H. Gu, Nano Res.2009,2, 365.
[36]A. J. Amali, R. K. Rana, Green Chem. 2009, 11,1781.
[37] S. M. Ribeiro, A. C. Serra, A.M. d’A. Rocha Gonsalves, App. Catal. 2011, A 399, 126.
[38] Z. Shen, Y. Chen, H. Frey, S-E. Stiriba, Macromol. 2006, 39, 2092.
[39] Y. Chi, S. T. Scroggins, E. Boz, J. M. J. Fre´chet, J. Ame. Chem. Soc, 2008,130, 17287.
[40]M-L. Wang, T-T. Jiang, Y. Lu, H-J. Liu, Y. Chen, J. Mater. Chem. A, 2013,1, 5923-5933.
[41] L. Martins, W. Hölderich, P. Hammer, D. Cardoso,J Catal.2010,271,220-227.
[42] D. Zois, C. Vartzouma, Y. Deligiannakis, N. Hadjiliadis, L. Casella, E. Monzani, J Mol Catal A: Chem.261 (2007) 306-317.
[43] M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal A: Chem. 2012,359, 74– 80.

[44] D. Zois, C. Vartzouma, Y. Deligiannakis, N. Hadjiliadis, L. Casella, E. Monzani, M. Louloudi, J. Mol. Catal. A: Chem. 2007,261, 306.
[46] D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 2010,47, 63.
[47] D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron, 2007,63, 3093.
[48] J.M. Khurana, B. Nand, P. Saluja, Tetrahedron, 2010, 66, 5637.
[49] Z. Deng, J. Wei, X. Xue, J. Wang, L. Chen, J Porous Mater. 2001,8, 37-42.

[50] P. Tartaj, Chem Commun. 2011,47, 256-258.
[51] HL .Pang, J. Liu, D. Hu, XH. Zhang, JH.Chen, Electrochim Acta. 2010,55, 6611-6616.