Fe3O4@SiO2@Am-PPC-SO3H] [HSO4]: A new magnetic solid acid nanocatalyst for the synthesis of benzoxazole derivatives

Document Type: Articles

Authors

1 Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran.

2 Department of Chemistry, Shoushtar Branch, Islamic Azad University, Shoushtar, Iran.

Abstract

A novel magnetite nanoparticle-based heterogeneous acidic catalyst [Fe3O4@SiO2@Am-PPC-SO3H] [HSO4] was successfully prepared and characterized by SEM, EDX, TGA, VSM and FT-IR techniques. The magnetically retrievable and sustainable catalyst was investigated in the reaction of aldehyde and o-aminophenol for the synthesis of benzoxazoles. The reactions occurred in water and produced the corresponding products in high yields. The catalyst could be readily separated by an external magnet and showed excellent reusability without significant loss of its activity.

Keywords


[1] B. Gilbert, J.E. Katz, J.D. Denlinger, Y. Yin, R. Falcone, G.A. Waychunas, J. Phys. Chem. C 114 (2010) 21994–22001.
[2] M. Sheykhan, L. Ma’mani, A. Ebrahimi, A. Heydari, J. Mol. Catal. A: Chem. 335 (2011) 253-261.
[3] B. Panella, A. Vargas, A. Baiker, J. Catal. 261 (2009) 88-93.
[4] A.R. Kiasat, S. Nazari, J. Mol. Catal. A: Chem. 365 (2012) 80-86.
[5] M. Mazloum-Ardakani, N. Rajabzadeh, A. Dehghani Firouzabadi, A. Benvidi, M. Abdollahi-Alibeik, Anal. Methods 6 (2014) 4462-4468.
[6] Y. Arum, Y. Song, J. Oh, Appl. Nanosci. 1 (2011) 237–246.
[7] J. Chen, X. Zhu. Food Chem. 200 (2016) 10–15.
[8] A. Amini, S. Sayyahi, S.J. Saghanezhad, N. Taheri, Catal. Commun. 78 (2016) 11–16.
[9] S. Sayyahi, S. Mozafari, S. J. Saghanezhad, Res. Chem. Intermed. 42 (2016) 511–518.
[10] A. Shouli, S. Menati, S. Sayyahi, C. R. Chim. 20 (2017) 765-772.
[11] Y.C. Sharma, B. Singh, Biofuels, Bioprod. Bioref. 5 (2011) 69-92.
[12] B. Karimi, F. Mansouri, H.M. Mirzaei, ChemCatChem 7 (2015) 1736-1095.
[13] M. Abdollahi-Alibeik, E. Heidari-Torkabad, C. R. Chim. 15 (2012) 517–523
[14] M.B. Gawande, A.K. Rathi, D. Nogueira, R.S. Varma, P.S. Branco, Green Chem. 15 (2013) 1895-1899
[15] S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L.V. Elst, R.N. Muller, Chem. Rev. 108 (2008) 2064-2110.
[16] C.Y. Jeong, J. Chio, M.H. Yoon, Eur. J. Pharmacol. 502 (2004) 205-211.
[17] A.D. Borthwick, D.E. Davies, P.F. Ertl, A.M. Exall, T.M. Haley, G.J. Hart, D.L. Jackson, N.R. Parry, A. Patikis, N. Trivedi, G. Weingarten, J.M. Woolven, J. Med. Chem. 46 (2003) 4428-4449.
[18] P-Y. Tong, Y-W. Lin, Inorg. Chim. Acta 362 (2009) 2033-2038.
[19] S.M. Rida, F.A. Ashour, S.A.M. El-Hawash, M.M. ElSemary, M.H. Badr, M.A. Shalaby, Eur. J. Med. Chem. 40 (2005) 949–59.
[20] S.R. Nagarajan, G.A. De Crescenzo, D.P. Getman, H. F. Lu, J. A. Sikorski, J. L. Walker, J.J. McDonald, K.A. Houseman, G. P. Kocan, N. Kishore, P.P. Mehta, C.L. Funkes-Shippy, L. Blystone, Bioorg. Med. Chem. 11 (2003) 4769-4777.
[21] R.C.M. Ferreira, M.M.M. Raposo, S.P.G. Costa, New J. Chem. 42 (2018) 3483-3492.
[22] P. Xue, P. Chen, J. Jia, Q. Xu, J. Sun, B. Yao, Z. Zhang, R. Lu, Chem. Commun. 50 (2014) 2569-2571.
[23] S. Heuser, M. Keenan A.G. Weichert, Tetrahedron Lett. 46 (2005) 9001-9004.
[24] R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti K.V. Srinivasan, J. Mol. Catal. A: Chem. 214 (2004) 155-160.
[25] A.K. Chakraborti, S. Rudrawar, G. Kaur, L. Sharma, Synlett (2004) 1533-1536.
[26] J. Azizian, P. Torabi, J. Noei, Tetrahedron Lett. 57 (2016) 185-188.
[27] S.M. Vahdat, S.G. Raz, S. Baghery, J. Chem. Sci. 126 (2014) 579-585.
[28] H. Sharma, N. Singh, D.O. Jang, Green Chem. 16 (2014) 4922-4930.
[29] A.V. Borhadea, B.K. Uphade, J. Iran. Chem. Soc. 6 (2016) 197-201.
[30] F. Karami Olia, S. Sayyahi, N. Taheri, C. R. Chim. 20 (2017) 370-376.
[31] A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem. 373 (2013) 46–54.
[32] Q. Zhang, H. Su, J. Luo, Y. Wei, Green. Chem. 14 (2012) 201–208.
[33] J.Z. Zhang, Q. Zhu, X. Huang, Synth. Commun. 32 (2002) 2175–2179.
[34] H. Naeimi, S. Rahmatinejad, Z. Sadat Nazifi, J. Taiwan Inst. Chem. Eng. 58 (2016) 1–7.
[35] S.S. Patil, V. D. Bobade, Synth. Commun. 40 (2010) 206–212.
[36] H.M. Bachhav, S.B. Bagat, V.N. Telvekar, Tetrahedron Lett. 52 (2011) 5697-5701.
[37] M. Kidwai, V. Bansal, A. Saxena, S. Aerryb, S. Mozumdar, Tetrahedron Lett. 47 (2006) 8049–8053.
[38] F. Chen, C. Shen, D. Yang, Tetrahedron Lett. 52 (2011) 2128–2131.
[39] J. Chang, K. Zhaob, S. Pan, Tetrahedron Lett. 43 (2002) 951–954.
[40] Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 5 (2003) 3713-3715.