Synthesis of 14H-dibenzo[a.j]xanthenes using Co@pyr/APTZCMNPs as a novel heterogeneous nanocatalyst

Iranian Journal of Catalysis

مقاله 7، دوره 7، شماره 3، آذر 2017، صفحه 225-232   

نوع مقاله: Articles

نویسندگان

Esmayeel Abbaspour-Gilandeh^* ؛ Mehraneh Aghaei-Hashjin

Young Researchers and Elites Club, Ardabil Branch, Islamic Azad University, Ardabil, Iran.

چکیده

Co@pyr/APTZCMNPs was synthesized, and some of its characteristic analyses, such as Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) were investigated. The results indicated that this heterogeneous catalyst was an excellent and reusable system to synthesize of 14H-dibenzo[a.j]xanthene derivatives through a one-pot condensation of β-naphthol and arylaldehydes at 90 °C under solvent-free conditions. Due to the magnetic nature of the catalyst, it could be easily recovered by an external magnetic field and comfortable reused at least five times without loss of its catalytic activity. High yields of the desired product, easy recovery of the catalyst and solvent-free conditions were some of the advantages of our methodology.

کلیدواژه‌ها

Heterogeneous catalyst؛ β-Naphthol؛ 14H-dibenzo[a.j]xanthenes؛ Solvent-free conditions

مراجع

[1] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J. M. Basset, Chem. Rev. 111 (2011) 3036-3075.
[2] N. Kalvari Janaki, R. Fazaeli, H. Alyari, Iran. J. Catal. 5 (2015) 49-56.
[3] R. Cano, D.J. Ramon, M. Yus, Tetrahedron 67 (2011) 5432-5436.
[4] B. Baruwati, V. Polshettiwar, R.S. Varma, Tetrahedron Lett. 50 (2009) 1215-1218.
[5] J. Liu, X. Peng, W. Sun, Y. Zhao, C. Xia, Org. Lett. 10 (2008) 3933-3936.
[6] M. Kooti, M. Afshari, Catal. Lett. 142 (2012) 319-325.
[7] S. Paul, J.H. Clark, J. Mol. Catal. A: Chem. 215 (2004) 107-111.
[8] S. Singh, B.C. Yadav, V.D. Gupta, P.K. Dwivedi, Mater. Res. Bull. 47 (2012) 3538-3547.
[9] S. Sultana, M. Zain Khan, K. Umar, J. Alloys Compd. 535 (2012) 44-49.
[10] J.Y. Ho, S.S. Deok, S.H. Woo, P.K. Soo, K.D. Wan, Nanotechnology 23 (2012) 125402-125407.
[11] C. Barcena, A.K. Sra, G.S. Chaubey, C. Khemtong, J.P. Liu, J. Gao, Chem. Commun. 19 (2008) 2224-2226.
[12] A. Jordan, R. Scholz, P. Wust, H. Fahling, F. Roland, J. Magn. Magn. Mater. 201 (1999) 413-419.
[13] T. Hideo, Jpn. Tokkyo Koho (1981) JP 56005480.
[14] R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G.J. Thomas, PCT Int. Appl. (1997) WO 9706178.
[15] J.P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[16] R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 45 (1998) 833-845.
[17] A. Banerjee, A.K. Mukherjee, Stain Technol. 56 (1981) 83-85.
[18] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
[19] C.G. Knight, T. Stephens, Biochem. J. 258 (1989) 683-689.
[20] R.N. Sen, N. Sarkar, J. Am. Chem. Soc. 47 (1925) 1079-1091.
[21] P. Papini, R. Cimmarusti, Gazz. Chim. Ital. 7 (1947) 142-145.
[22] B. Rajitha, B. Sunil Kumar, Y.T. Reddy, Y.N. Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691-8693.
[23] K. Ota, T. Kito, Bull. Chem. Soc. Jpn. 49 (1976) 1167-1168.
[24] L. Nagarapu, S. Kantevari, V.C. Mahankhali, S. Apuri. Catal. Commun. 8 (2007) 1173-1177.
[25] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B. Rao-Vittal, J. Mol. Catal. A: Chem. 255 (2006) 74-77.
[26] A. Saini, S. Kumar, J.S. Sandhu, Synlett (2006) 1928-1932.
[27] S. KO, C.F. Yao, Tetrahedron Lett. 47 (2006) 8827-8829.
[28] J.V. Madhav, V.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kumar, P.A. Crooks, B. Rajitha, J. Mol. Catal. A: Chem. 304 (2009) 85-87.
[29] E. Abbaspour-Gilandeh, M. Aghaei-Hashjin, A. Yahyazadeh, H. Salemi, RSC Adv. 6 (2016) 55444-55462.
[30] E. Abbaspour-Gilandeh, S.C. Azimi, A. Mohammadi-Barkchai, RSC Adv. 4 (2014) 54854-54863.
[31] E. Abbaspour-Gilandeh, M. Aghaei-Hashjin, P. Jahanshahi, M. Hoseininezhad, Monatsh Chem. 148 (2017) 731-738.
[32] K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett. 54 (2013) 4633-4636.
[33] A. Khorshidi, K. Tabatabaeian, H. Azizi, M. Aghaei-Hashjin, E. Abbaspour-Gilandeh, RSC Adv. 7 (2017) 17732-17740.
[34] E. Abbaspour-Gilandeh, S.C. Azimi, K. Rad-Moghadam, A. Mohammadi-Barkchai, Iran. J. Catal. 3 (2013) 15-20
[35] E. Abbaspour-Gilandeh, S.C. Azimi, K. Rad-Moghadam, A. Mohammadi-Barkchai, Iran. J. Catal. 2 (2013) 91-97.
[36] D. Fang, K. Gong, Z.L. Liu, Catal. Lett. 127 (2009) 291-295.
[37] A. Khoramabadi-Zad, Z. Kazemi, H. Amiri Rudbari, J. Korean Chem. Soc. 46 (2002) 541-544.
[38] S. Kantevari, M. Venu Chary, A.P. Rudra Das, S.V.N. Vuppalapati, N. Lingaiah, Catal. Commun. 9 (2008) 1575-1578.
[39] S. Rostamizadeh, N. Shadjou, A.M. Amani, S. Balalaie, Chin. Chem. Lett. 19 (2008) 1151-1155.
[40] A.R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett (2005) 955-958.
[41] A.K. Bhattacharya, K.C. Rana, M. Mujahid, I. Sehar, A. K. Saxena, Bioorg. Med. Chem. Lett. 19 (2009) 5590-5593.
[42] M. Hong, C. Cai, J. Fluorine Chem. 130 (2009) 989-992.
[43] B. Rajitha, B. Sunil Kumar, Y. Thirupathi Reddy, Y. Narasimha Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691-8693.