-Fe2O3@SiO2-PW12 nanoparticles: Highly efficient catalysts for the synthesis of pyrazoline derivatives

محورهای موضوعی : Iranian Journal of Catalysis

Hamid Aliyan ¹ , Razieh Fazaeli ² , Nafiseh Tajsaeed ³

1 - Department of Chemistry, Islamic Azad University, Shahreza Branch, Shahreza, Iran.
2 - Department of Chemistry, Shahreza Branch, Islamic Azad University, 86145-311, Iran.
3 - Department of Chemistry, Shahreza Branch, Islamic Azad University, 86145-311, Iran.

تاریخ دریافت : 1391/10/28 تاریخ پذیرش : 1392/05/30 تاریخ انتشار : 1392/03/11

کلید واژه: Heterogeneous catalysis, Silica-encapsulated -Fe2O3 nanoparticles, Pyrazoline, Phenyl hydrazine, Chalcone,

چکیده مقاله :

A new type of magnetically-recoverable catalyst was synthesized by the immobilization of H3PW12O40 on the surface of silica-encapsulated -Fe2O3 nanoparticles. A series of novel 1,3,5-triaryl pyrazoline derivatives has been synthesized by the reaction of chalcone and phenylhydrazine in the presence of the -Fe2O3@SiO2-PW12nanoparticles, in high yields. The structures of compounds obtained were determined by IR and 1H NMR spectra. -Fe2O3@SiO2-PW12was recycled and no appreciable change in activity was noticed after three cycles.

منابع و مأخذ:

[1] R.H. Wiley, Ed.; Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings; in the Chemistry of Heterocyclic Compounds; Weissberger A, Ed.; Interscience Publishers: New York, 1967; Vol. 22, p 180.
[2] K. Manna, Y.K. Agrawal. Bioorg. Med. Chem. Lett., 19 (2009) 2688-2692.
[3] M. Abid, A.R. Bhat, V. Athar, A. Azam, Eur. J. Med. Chem., 44 (2009) 417-425.
[4] Z.A. Kaplancikli, G. Turan-Zitouni, A. Özdemir, Ö. D. Can, P. Chevallet. Eur. J. Med. Chem., 44 (2009) 2606-2610.
[5] D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, L. Zaprutko, R. Lesyk, Eur. J. Med. Chem., 44 (2009) 1396-1404.
[6] N. Gokhan-Kelekci, S. Koyunoğlu, S. Yabanoğlu, K. Yelekçi, Ö. Özgen, G. Uçar, K. Erol, E.  Kendi, A. Yeşilada. Bioorg. Med. Chem., 17 (2009) 675-689.
[7] Barsoum F F, Hosni H M, Girgis A S. Bioorg Med Chem, , 14 (2006) 3929-3937.
[8] S.J. Ji, H.B. Shi. Dyes Pigments, 70 (2006) 246-250.
[9] X.Q. Wei, G. Yang, J.B. Cheng, Z.Y. Lu, M.G. Xie, Opt. Mater., 29 (2007) 936-940.
[10] J.-T. Li, X.-H. Zhang, Z. –P. Lin, Beilstein J. Org. Chem., 3 (2007) 13-16.
[11] A. Levai, ARKIVOC,  No.ix (2005) 344-352.
[12] M. Kidwai, S. Kukreja, R. Thakur. Lett. Org. Chem., 3 (2006) 135-139.
[13] R. Fazaeli, H. Aliyan, M. Bordbar, E. Mohammadi, The Open Catal. J., 3 (2010) 79-82.
[14] R. Fazaeli, H. Aliyan, S. Mallakpour, Z. Rafiee, M. Bordbar. Chin. J. Catal. 32 (2011) 582-588.
 
[15] S. Safaee, I. Mohammadpour-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal., 345 (2012) 3095-3104.
[16] I. V. Kozhevnikov, I. V.;Sinnema, A.; R. J. J. Jansen, R. J. J.; Bekkum, H. Catal. Lett., 27 (1994) 187-197.
[17] G.D. Yadav, N. Kirthivasan, Appl. Catal. A: Gen., 154 (1997) 29-53.
[18] M. Misono, Chem. Commun. (2001) 1141-1442.
[19] I. Kozhevnikov, “Catalysts for Fine Chemical Synthesis, Catalysis by polyoxometalates”, Vol 2. Wiley, NewYork.
[20] E. Rafiee, S. Eavani, F. KhajooeiNejad and M. Joshaghani, Tetrahedron, 66 (2010) 6858-6863.
[21] H. Zeng, H. Li and H. Shao, Ultrason. Sonochem., 16 (2009) 758-762.
[22] R. H. Wiley, C.H. Jarboe, F.N. Hayes, E. Hansbury, J.T. Nielsen, P.X. Callahan, M.C. Sellars.  J. Org. Chem., 23 (1958) 732-738.
[23] E. Darezereshki, M. Ranjbar and F. Bakhtiari, J. Alloys Compd., 502 (2010) 257-260.
[24] E. Rafiee, S.Eavani, Green Chem., 13 (2011) 2116-2122.
[25] C. He, T. Sasaki, Y. Shimizu andN.Koshizaki, Appl. Surf. Sci., 254 (2008) 2196-2202.
[26] K. C. Barick, B. S. D. Ch. S. Varaprasad and D. Bahadur, J. Non-Cryst. Solids, 356 (2010) 153-159.
[27] R. Fazaeli,H. Aliyan, S. Tangestaninejad, E. Mohammadi, M. Bordbar, Chinese J. Catal., 33 (2012) 237-246.
[28] Z.P. Lin, J.-T. Lie., E. J. Chem., 9 (2012) 267-271.