Fe3O4@SiO2 nanoparticles: An efficient, green and magnetically reusable catalyst for the one-pot synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-dione derivatives

Document Type: Articles

Authors

Department of Chemistry, Qom Branch, Islamic Azad University, Qom, P.O. Box 37491-13191. R. Iran

Abstract

An efficient and eco-friendly method for the one-pot synthesis of 14-aryl-14H-dibenzo [a,i]xanthene-8,13-dione derivatives has been developed in the presence of Fe3O4@SiO2 core-shell nanoparticles. The multi-component reactions of 2-hydroxy-1,4-naphthoquinone, β-naphthol and aldehydes were efficiently catalyzed using novel nano-scale materials under reflux conditions. The present method offers several advantages such as environmentally benign, simple work-up, excellent yield of products, short reaction times, little catalyst loading and facile catalyst separation. The nanomagnetic catalyst could be readily recovered using a simple external magnet and reused several times without any significant loss in activity. The catalyst was fully characterized by FT-IR, SEM, XRD, EDX and VSM analysis.

Keywords


[1] S.M. Moghimi, A.C.H. Hunter, J.C. Murray, Pharm. Rev. 53 (2001) 283-318.
[2] A.S.G. Curtis, C. Wilkinson, Trends Biotech. 19 (2001) 97-101.
[3] J.M. Wilkinson, Med. Device Technol. 14 (2003) 29-31.
[4] M.G. Dekamin, Z. Mokhtari, Z. Karimi, Sci. Iran. Trans. C 18 (2011) 1356-1364.
[5] Z. Bing, H. Scott, R. Raja, G.A. Somorjai, Nanotechnology in Catalysis, Springer, Ottawa, 2007.
[6] Y. Min, M. Akbulut, K. Kristiansen, Y. Golan, J. Israelachvili, Nat. Mater. 7 (2008) 527-538.
[7] (a) M.H. Alizadeh, H. Razavi, F.F. Bamoharram, J. Mol. Catal. A: Chem. 206 (2003) 89-93. (b) G.M. Ziarani, A. Badiei, F. Shahjafari, T. Pourjafar, S. Afr. J. Chem. 65 (2012) 10-13.
[8] N. Ahmed, J.E. Van Lier, Tetrahedron Lett. 47 (2006) 2725-2729.
[9] Q. Dang, B.S. Brown, M.D. Erion, Tetrahedron Lett. 41 (2000) 6559-6562.
[10] Y.H. Deng, W.L. Yang, C.C. Wang, S. K. Fu, Adv. Mater. 15 (2003) 1729-1732.
[11] L.M. Liz-Marzán, M. Giersig, P. Mulvaney, Langmuir 12 (1996) 4329-4335.
[12] G. Eyanom, N. Blanchard, M. Toumi, Chem. Rev. 108 (2008) 3054-3131.
[13] (a) L. A. Thompson, J. A. Ellman, Chem. Rev. 96 (1996) 555-600. (b) G. I. Shakibaei, A. Feiz, A. Bazgir, C.R. Chim. 14 (2011) 556-562.
[14] (a) T. Hideo, J. Teruomi, Jpn. Tokkyo Koho (1981) JP56005480. (b) V. Peres, T. Nagem, F.F. de Oliveira, Phytochemistry 5 (2000) 683-710.
[15] (a) R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G.J. Thomas, PCT Int. Appl. (1997) WO9706178. (b) G.J. Bennett, H.H. Lee, Phytochemistry 28 (1989) 967-998.
[16] (a) H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag, A.B. A. El-Gazzar, Bioorg. Med. Chem. Lett. 18 (2008) 4538-4543. (b) M.M.M. Pinto, M.E. Sousa, M.S.J. Nascimento, Curr. Med. Chem. 12 (2005) 2517-2538.
[17] M. Behforouz, J. Haddad, W. Cai, Z. Gu, J. Org. Chem. 63 (1998) 343-346.
[18] M.F. Sartori, Chem. Rev. 63 (1963) 279-296.
[19] A.S. Hammam, M.S.K. Youssef, M. Radwansh, M.A. Abdel-Rahman, Bull. Korean Chem. Soc. 25 (2004) 779-785.
[20] C.W. Kuo, J.M. Fang Synth, Chem. Commun. 31 (2001) 877-892.
[21] A. Jha, J. Beal, Tetrahedron Lett. 45 (2004) 8999-9001.
[22] R. Kumar, G.C. Nandi, R.K. Verma, M.S. Singh, Tetrahedron Lett. 51 (2010) 442-445.
[23] N.G. Khaligh, Catal. Sci. Technol. 2 (2012) 2211-2215.
[24] L. Q. Wu, Y.F. Wu, C.G. Yang, L.M. Yang, L.J. Yang, J. Braz. Chem. Soc. 21 (2010) 941-945.
[25] K.B. Suresh, P.A. Crooks, B. Rajitha, Adv. Appl. Sci. Res. 3 (2012) 1-5.
[26] L. Wu, J. Zhang, L. Fang, C. Yang, F. Yan, Dyes Pigm. 86 (2010) 93-96.
[27] S. Chao, G. Lu, L. Wu, Asian J. Chem. 23 (2011) 3865-3869.
[28] V. Srinivas, R. Rajeswar, V. Synth. Commun. 42 (2012) 388-393.
[29] J.M. Khurana, A. Chaudhary, A. Lumb, B. Nand, Can. J. Chem. 90 (2012) 739-746.
[30] J. Safaei-Ghomi, S. Zahedi, M.A. Ghasemzadeh, Iran. J. Catal. 2 (2012) 27-30.
[31] J. Safaei-Ghomi, M.A. Ghasemzadeh, J. Chem. Sci. 125 (2013) 1003-1008.
[32] M.A. Ghasemzadeh, J. Safaei-Ghomi, J. Chem. Res. 38 (2014) 313-316.
[33] M.A. Ghasemzadeh, J. Safaei-Ghomi, Acta Chim. Slov. 62 (2015) 103-110.
[34] M.A. Ghasemzadeh, J. Safaei-Ghomi, S. Zahedi, J. Serb. Chem. Soc. 78 (2013) 769-779.
[35] M.A. Ghasemzadeh, J. Safaei-Ghomi, H. Molaei, C.R. Chim. 15 (2012) 969-974.
[36] M.A. Ghasemzadeh, J. Safaei-Ghomi, J. Chem. Res. 38 (2014) 313-316.
[37] H.Y. Lu, S.H. Yang, J. Deng, Z.H. Zhang, Aust. J. Chem. 63 (2010) 1290-1296.
[38] X.Q. Xu, C.H. Deng, M.X. Gao, W.J. Yu, P.Y. Yang, X.M. Zhang, Adv. Mater. 18 (2006) 3289-3293.