Iranian Journal of Chemistry

Iranian Journal of Chemistry

ZnS-ZnFe2O4: Magnetic nanocatalyst for efficient synthesis of tetrasubstituted benzimidazoles

Document Type : Original Article

Authors
Ali Maleki 1
fereshte hassanzadeh Afruzi 2
zahra varzi 3
1 Associate Professor, Department of Chemistry, Iran University of Science and Technology Tehran, Iran
2 PhD Student, Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
3 M.Sc. Student, Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
10.22036/ijc.2019.142793.1024
Abstract
Catalysts in chemical reactions improve the reaction conditions, increase the speed and yield of the products. So, they play a prominent role in various industries such as the chemical industry, petroleum industry, and pharmaceutical chemistry. In this work, an efficient and co-friendly method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles via a four-component condensation of benzil, aldehydes, primary amines and ammonium acetate in the presence of a magnetic nanocatalyst, ZnS-ZnFe2O4, in ethanol under refluxing conditions is presented. Magnetic ZnS-ZnFe2O4 was prepared via a simple method and characterized by energy-dispersive X-ray analysis (EDAX), field-emission scanning electron microscopy (FESEM), X-Ray diffraction pattern (XRD) and vibrating sample magnetometer (VSM). This protocol has advantages such as high yields of the products, use of a green solvent, simple and chromatography-free work-up procedure. Most importantly, the catalyst can be conveniently recovered from the reaction mixture by using external magnet and reused for at least three times without significant decrease in catalytic activity.

Graphical Abstract

ZnS-ZnFe2O4: Magnetic nanocatalyst for efficient synthesis of tetrasubstituted benzimidazoles
Keywords
Tetrasubstituted benzimidazoles
multicomponent reaction
recyclable magnetic nanocatalyst
green chemistry
Subjects
1) A. Domling, W. Wang, K. Wang, Chem. Rev., 112, 3083 (2008).
2) M. Benaglia, Recoverable and Recyclable Catalysts, John Wiley & Sons. 2009.
3) S. Wittmann, A. Schätz, R.N. Grass, W.J. Stark, O. Reiser, Angew. Chem. Int. Ed., 49, 1867-1870 (2010).
4) A. Maleki, R. Paydara, RSC Adv., 5, 33177-33184 (2015).
5) G.A. Somorjai, H. Frei, J.Y. Park, J. Am. Chem. Soc., 131, 16589–16605 (2009).
6) N. Erfaninia, R. Tayebee, E.L. Foletto, M.M. Amini, M. Dusek, F.M. Zonoz, Appl. Organomet. Chem., 32, 4047 (2017).
7) A.M. Gama, M.C. Rezende, Mater. Res., 16, 997-1001 (2013).
8) A. Teimouri, A.N. Chermahini, J. Mol. Catal. A: Chem., 346, 39-45 (2011).
9) H. Aghahosseini, A. Ramazani, K. Ślepokura, T. Lis, J. Colloid Interface Sci. 511, 222-232 (2018).
10) A.R. Moosavi-Zare, Z. Asgari, A. Zare, M.A. Zolfigol, M. Shekouhy, RSC Adv., 4, 60636-60639 (2014).
11) S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem., 266, 109–113 (2007).
12) A.V. Borhade, D.R. Tope, S.G. Git, Arab. J. Chem., 10, S559-S567 (2017).
13) M. Esmaeilpour, J. Javidi, F. Dehghani, S. Zahmatkesh, Res. Chem. Intermed., 43, 163–185 (2017).
14) J.J. Gabla, S.R. Mistry, K.C. Maheria, Catal. Sci. Technol., 7, 5154-5167 (2017).
15) X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, H.L. Ye, Chin. Chem. Lett., 20, 44–47 (2009).
16) B.F. Mirjalili, A.H. Bamoniri, L. Zamani, Sci. Iran., 19, 565–568 (2011).
17) M.M. Heravi, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A: Chem., 263, 112–114 (2007).
18) B. Sadeghi, B.F. Mirjalili, M. M.Hashemi, Tetrahedron Lett., 49, 2575-2577 (2008).
19) M. Salimi, M.A. Nasseri, T.D. Chapesshloo, B. Zakerinasab, RSC Adv., 5, 33974 (2015).
 
Iranian Journal of Chemistry
Volume 2, Issue 1 - Serial Number 2
September 2019
Pages 43-51

  • Receive Date 01 August 2018
  • Revise Date 28 September 2018
  • Accept Date 14 June 2019