Document Type : Original Research Article

Author

Shahreza Branch, Islamic Azad University

Abstract

H3PW12O40 (PW12) was immobilized over mesoporous alumina through the reaction of mesoporous alumina functionalized 3-aminopropyl triethoxy silane (3-APTES) and PW12. The surface properties of the functionalized nanocomposite was analyzed by a series of characterization techniques like elemental analysis, FTIR and XRD. XRD and adsorption–desorption analysis shows that the mesostructure of silica remains intact after various modifications, while spectral technique show the successful grafting of the neat PW12 inside the porous silica support. 3-Alkylindole derivatives were produced by ring opening of epoxides in the presence of PW12-APTES@ SBA-15 nanocomposites as an efficient catalyst. The catalyst can be reused for several times but it will be less active.

Graphical Abstract

Friedel-Crafts alkylation of indoles with epoxides using PW12-APTES@SBA-15

Keywords

Main Subjects

[1] C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature, 1992, 359, 710-712.
[2] Q. Huo, D.I. Margolese, V. Ciesla, P. Feng, T.E. Gier, P. Sieger, R. Leon, P.M. Petroff, F. Schuth, G.D. Stucky, Nature, 1994,  368 , 317-321.
[3] A. Sayari, P. Liu, Microporous Mater., 1997, 12, 149-296.
[4] M. Chidambaram, D.C. Ferre, A.P. Singh, B.G. Anderson, J. Catal., 2003, 220, 442-456.
[5] Y. Iwasawa, Tailored Metal Catalysts, Springer, Reidel, Holand, 1986, 141-182
[6] A. Kozlov, K. Asakura, Y. Iwasawa, Microporous Mesoporous Mater., 1998, 21, 571-579.
[7] J.T. Li, H.G. Dai, Z.P.Lin, Prog. Chem., 2007, 19, 751-761.
[8] Y. Tomioka, K. Ohkubo, H.J. Maruoka, Heterocycl. Chem., 2007, 44, 419-424.
[9] C. Unaleroglu, C.; Aytac, S.; Temelli, B. Heterocycles, 2007, 71, 2427-2440.
[10] J.W. Huffman, L.W. Padgett, M.L. Isherwood, J.L. Wiley, B.R. Martin, Bioorg. Med. Chem. Lett., 2006, 16, 5432-5435.
[11] X.  Zou, X. Wang, C. Cheng, L. Kong, H. Mao, Tetrahedron Lett., 2006, 47, 3767-3771.
[12] S. Lin, T. You, Tetrahedron, 2009, 65, 1010-1016.
[13] K. Tabatabaeian, M. Mamaghani, N.O.  Mahmoodi, A.  Khorshidi, Tetrahedron Lett., 2008, 49, 1450-1454.
[14] B. Das, P. Thirupathi, R.A. Kumar, K.R.  Reddy, Catal. Commun., 2008, 9, 635-638.
[15] Y.H. Liu, Q.S. Liu, Z.H. Zhang, Tetrahedron Lett., 2009, 50, 916-921.
[16] N. Azizi, S. Mehrazma, M.R. Saidi, Can. J. Chem., 2006, 84, 800-803.
[17] A. Heydari, M. Mehrdad, A.  Maleki, N. Ahmadi, Synthesis, 2004, 10, 1557-1558.
[18] J.S. Yadav, B.V.S. Reddy, G.J. Parimala, Chem. Res. Synop., 2003, 2, 78-81.
[19] M. Westermaier, H. Mayr, Chem. Eur. J., 2008, 14, 1638-1647.
[20] H. Kotsuki, M. Teraguchi, N. Shimomoto, M. Ochi, Tetrahedron Lett., 1996, 37, 3727-3730.
[21] J.S. Yadav, B.V.S. Reddy, S. Araham, G. Sabitha, Synlett, 2002, 9, 1550-1552.
[22] M. Bandini, P.G. Cozzi, P. Melchiorre, A.U. Ronchi, J. Org. Chem., 2002, 67, 5386-5389.
[23] B.P. Bandgar, A.V. Patil, Tetrahedron Lett., 2007, 48, 173-176.
[24] T. Hudlicky, U. Rinner, K.J. Finn, I. Ghiviriga, J. Org. Chem., 2005, 70, 3490-3499.
[25] M.H. Sarvari, G. Parhizgar, Green Chem. Lett. Rev., 2012, 1-11.
[26] C. Ge, R. R. Liu, J.R. Gao, Y.X.  Jia, Org. Lett. 2016, DOI: 0.1021/acs.orglett.6b01317
[27] D. Lianga, X. Lia, W. Zhanga,Y. Lia, M. Zhanga, P. Chengb Tetrahedron Lett., 2016, 57, 1027-30.
[28] M.M.  Nasefab, M. Zakeria,  J. Asadic, E. A. Lotfab, A. Ahmada, R. Malakootid Green Chemistry Letters and Reviews, 2016, 9,76-84.
[29] A. Taheri,  B. Lai, C. Chenga  Y.  Gu, Green Chem., 2015, 17, 812-816.
[30] B. Bi, Q.X. Lou, Y.Y. Ding, S.W. Chen, S.S. Zhang, W.H. Hu, J.L. Zhao, Org. Lett., 2015, 17, 540–543
[31] T. Courant, S. Kumarn, L. He, P.  Retailleau1, G. Masson, Adv. Synth. Catal., 2013, 355, 836-840.
[32] H. Kotsuki, K. Hayashida, T. Shimanouchi, H. Nishizawa, J. Org. Chem., 1996, 61, 984-990.
[33] H. Kotsuki, M. Nishiuchi, S. Kobayashi, H. Nishizawa, J. Org. Chem., 1990, 55, 2969-2972.
[34] M.L. Kantam, R. Chakravarti, B. Sreedhar, S. Bhargava, Synlett, 2008, 10, 1449-1454.
[35] R. Fazaeli, S. Tangestaninejad, H. Aliyan, Appl. Catal. A., 2007, 318, 218-226.
[36] R. Fazaeli, H. Aliyan, Appl. Catal. A., 2007, 331, 78-83.
[37] R. Fazaeli, H. Aliyan, Appl. Catal. A., 2009, 353, 74-79.
[38] M. Sun, J.Z. Zhang, C.J. Cao, Q.H. Zhang, Y. Wang, H.L. Wan. Appl. Catal. A., 2008, 349, 212-221.
[39] V.D. Chaube, S. Shylesh, A.P. Singh, J. Mol. Catal: Chem., 2005, 241, 79–87.
[40] I. Diaz, C. Marquez-Alvarez, F. Mahino, J. Perez-Periente, E. Sastre, J. Catal., 2000, 193, 283–294.
[41] B.H. Wouters, T. Chen, M. Dewilde, P.J. Grobet, Micropor. Mesopor. Mater., 2001, 45,  453–457.
[42] A.B. Jarze˛bski, K. Szyman´ ska, J. Bryjak, J. Mrowiec-Białon´, Catal. Today, 2007, 124, 2–10.
[43] Y. Guo, D. Li, C. Hu, Y. Wang, E. Wang, Y. Zhou, S. Feng, Appl. Catal. B: Env., 2001,  30, 337-349.
[44] J. Aburto, M. Ayala, I. Bustos-Jaimes, C. Montiel, E. Terre´ s, J.M. Domı´nguez, E. Torres, Micropor. Mesopor. Mater., 2005, 83, 193–200.
[45] I.V. Kozhevnikov, Catalysis by Polyoxometalates, Wiley, England, 2002.
[46] V.D. Chaube, S. Shylesh, A.P. Singh, J. Mol. Catal. A: Chem., 2005, 241, 79–87.
[47] K. Kannan, R.V. Jasra, J. Mol. Catal. B: Enzym., 2009, 56, 34–40.