Synthesis of 2,4,5-triaryl-1H-imidazoles using a potent, green and reusable nano catalyst (FHS/SiO2)
محورهای موضوعی : Iranian Journal of CatalysisMehdi Bakavoli 1 , Hossein Eshghi 2 , Ali Mohammadi 3 , Hassanali Moradi 4 , Javad Ebrahimi 5
1 - Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436, Mashhad, Iran.
2 - Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436, Mashhad, Iran.
3 - Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436, Mashhad, Iran.
4 - Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436, Mashhad, Iran.
5 - Young Researchers Club, Islamic Azad University, Mashhad Branch
کلید واژه: Heterogeneous catalyst, Nano Catalyst, 2, 4, 5-Trisubstituted imidazoles, Solvent-free synthesis, Ferric hydrogen sulfate,
چکیده مقاله :
A simple, green and efficient method for synthesis of 2,4,5-trisubstituted imidazoles is described via three-component cyclocondensation of benzil or benzoin, aldehyde and ammonium acetate by using the nano SiO2-supported ferric hydrogen sulfate (FHS/SiO2), as a catalyst, under solvent-free conditions. The nano SiO2 support and catalyst were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM) and IR spectroscopy. In this project, the optimum conditions such as: reaction temperature, reaction time and amount of catalyst were investigated. The major advantages of the present method are high yields, shorter reaction times, easy work-up, purification of products by non-chromatographic method and the reusability of the catalyst.
[1] L.S. Gadekar, S.R. Mane, S.S. Katkar, B.R. Arbad, M.K. Lande, Cent. Eur. J. Chem. 7 (2009) 550-554.
[2] B. Radziszewski, Chem. Ber. 15 (1882) 1493–
1496.
[3] F. Japp, H. Robinson, Chem. Ber. 15 (1882) 1268–
1270.
[4] G. Sharma, Y. Jyothi, P. Lakshmi, Synth. Commun. 36 (2006) 2991–3000.
[5] S. Balalaie, A. Arabanian, M. Hashtroudi, Monatsh. Chem. 131 (2000) 945–948.
[6] J. Sangshetti, N. Kokare, A. Kotharkar, D. Shinde, Monatsh. Chem. 139 (2008) 125-127.
[7] A. Mohammed, N. Kokare, J. Sangshetti, D. Shinde, J. Korean Chem. Soc. 51 (2007) 418–422.
[8] M. Kidwai, P. Mothsra, V. Bansal, R. Goyal, Monatsh. Chem. 137 (2006) 1189–1194.
[9] J.N. Sangshetti, N.D. Kakare, S.A. Kotharkar, D.B. Shinde, J. Chem. Sci. 120 (2008) 463–467.
[10] N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Synthesis (2007) 2829–2834.
[11] S. Siddiqui, U. Narkhede, S. Palimkar, T. Daniel, R. Lahoti, K. Srinivasan, Tetrahedron 61 (2005) 3539-3546.
[12] J.F. Zhou, Y.Z. Song, Y.L. Zhu, S.J. Tu, Synth. Commun. 35 (2005) 1369–1373.
[13] A. Mohammadi, H. Keshvari, R. Sandaroos, B. Maleki, H. Rouhi, H. Moradi, Z. Sepehr, S. Damavandi, Appl. Catal. A: Gen. 429– 430 (2012) 73-78.
[14] B.F. Mirjalili, A. Bamoniri, M.A. Mirhoseini, Sci. Iran. 20 (2013) 587–591.
[15] H. Eshghi, M. Bakavoli, H. Moradi, Chin. Chem. Lett. 20 (2009) 663–667.
[16] H. Eshghi, S.M. Seyedi, E. Safaei, M. Vakili, A. Farhadipour, M. Bayat‐Mokhtari, J. Mol. Catal. A: Chem. 363‐364 (2012) 430-436.
[17] H. Eshghi, M. Rahimizadeh, M. Hosseini, A. Javadian‐Saraf, Monatsh. Chem. 144 (2013) 197-203.
[18] A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi, F. Moeinpour, M. Bakavoli, Chin. J. Catal. 35 (2014) 376-382.
[19] H. Eshghi, J. Chin. Chem. Soc. 53 (2006) 987-999.
[20] M. Kidwai, P. Mothsra, V. Bansal, R. Goyal, Monatsh. Chem. 137 (2006) 1189–1194.
[21] H. Zang, Q. Su, Y. Mo, B.W. Cheng, S. Jun, Ultrason. Sonochem. 17 (2010) 749-751.
[22] B.F. Mirjalili, A. Bamoniri, N. Mohaghegh, Curr. Chem. Lett. 2 (2013) 35-42.
[23] S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65 (2009) 10155-10161.
[24] F.F. Bamoharram, M.M. Heravi, J. Ebrahimi, A. Ahmadpour, M. Zebarjad, Chin. J. Catal. 32 (2011) 782-788.
[25] A. Mohammadi, H. Keshvari, R. Sandaroos, H. Rouhi, Z. Sepehr, J. Chem. Sci. 124 (2012) 717-722.
