Ultrasound based method for one-pot synthesis of substituted imidazoles using SiO2-OSbCl2 as highly effective and reusable catalyst
الموضوعات : Iranian Journal of CatalysisJavad Safari 1 , Zohre Zarnegar 2 , Simin Naseh 3 , Zahra Akbari 4
1 - Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R., Iran.
2 - Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R., Iran.
3 - Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R., Iran.
4 - Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R., Iran.
الکلمات المفتاحية: Heterogeneous catalyst, Imidazoles, SiO2-OSbCl2, Lewis acid, Sonication,
ملخص المقالة :
A simple highly versatile and efficient sonochemical synthesis of 1,2,4,5-tetrasubstituted and 2,4,5-trisubstituted imidazoles is achieved by condensation of 1,2-dicarbonyl compound, aldehyde, ammonium acetate and primary amine using antimony trichloride immobilized on silica gel (SiO2-OSbCl2) as a catalyst in ethanol at moderate temperature. Operational simplicity, practicability and applicability to various substrates make this method an interesting alternative to previously applied procedures. From the environmental standpoint, this eco-friendly green catalyst is stable, highly active, easy to prepare and handle.
[1] R.S. Varma, Green Chem. 1 (1999) 43-55.
[2] J.H. Clark, Acc. Chem. Res. 35 (2002) 791-797.
[3] A. Corma, H. Garcia, Chem. Rev. 103 (2003) 4307-4365.
[4] G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev. 104 (2004) 199-250.
[5] L.F. Zhang, S.T. Yang, Russ. J. Org. Chem. 45 (2009) 18-21.
[6] H.R. Darabi, K. Aghapoor, F. Mohsenzadeh, F. Taala, N. Asadollahnejad, A. Badiei, Catal. Lett. 133 (2009) 84-89.
[7] Z.H. Zhang, J.J. Li, T.S. Li, Ultrason. Sonochem. 15 (2008) 673-676.
[8] G. Maiti, P. Kundu, Tetrahedron Lett. 47 (2006) 5733-5736.
[9] A.K. Mitra, N. Karchaudhuri, A. De, J. Indian Chem. Soc. 82 (2005) 177-179.
[10] A. Srinivasa, B.P. Nandeshwarappa, B.M. Kiran, K.M. Mahadevan, Phosphorus, Sulfur, Silicon Relat. Elem. 182 (2007) 2243-2249.
[11] G. Maiti, P. Kundu, Synth. Commun. 37 (2008) 2309-2316.
[12] M.C. Singh, R.K. Peddinti, Tetrahedron Lett. 48 (2007) 7354-7357.
[13] H.R. Darabi, A. Mirzaee, M.R. Poorheravi, F. Mohsenzadeh, H. Taherzadeh, Y. Balavar, K. Aghapoor, N. Asadollahnejad, Environ. Chem. Lett. 10 (2012) 5-12.
[14] K.H. Bleicher, F. Gerber, Y. Wutherich, Tetrahedron Lett. 43 (2002) 7687-7690.
[15] J. Safari, Sh. Dehghan Khalili, M. Rezaei, S.H. Banitaba, F. Meshkani, Monatsh. Chem. 141 (2010) 1339-1345.
[16] S. Kantevari, C.K.S. Nair, M. Pardhasaradhi, J. Heterocycl. Chem. 43 (2006) 1353-1556.
[17] M. Misono, Chem. Commun. 44 (2001) 1141-1152.
[18] S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem. 266 (2007) 109-113.
[19] U. Ucucu, N.G. Karaburun, I. Iskdag, Farmaco. 56 (2001) 285-290.
[20] S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron. 61 (2005) 3539-3546.
[21] J. Wang, R. Mason, D.V. Derveer, K. Feng, X.R. Bu, J. Org. Chem. 68 (2003) 5415-5418.
[22] A. Shaabani, A. Rahmati, J. Mol. Catal. A: Chem. 249 (2006) 246-248.
[23] S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49 (2008) 2216-2220.
[24] J.N. Sangshetti, N.D. Kokare, S.A. Kothrkara, D.B. Shinde, J. Chem. Sci. 120 (2008) 463-467.
[25] M.M. Heravi, K. Bakhtiari, H.A. Oskooie, S. Taheri, J. Mol. Catal. A: Chem. 263 (2007) 279-281.
[26] S. Balalaie, A. Arabanian, Green Chem. 2 (2008) 274-276.
[27] M.M. Heravi, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A: Chem. 263 (2008) 112-114.
[28] B. Sadeghi, B.B.F. Mirjalili, M.M. Hashemi, Tetrahedron Lett. 49 (2008) 2575-2577.
[29] A.R. Karimi, Z. Alimohammadi, J. Azizian, A.A. Mohammadi, M.R. Mohammadizadeh, Catal. Commun. 7 (2008) 728-732.
[30] S. Kantevari, S.V.N. Vuppa-lapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem. 266 (2007) 109-113.
[31] S. Balalaie, M.M. Hashemi, M. Akhbari, Tetrahedron Lett. 44 (2003) 1709-1711.
[32] I. Lantos, W.Y. Zhang, X. Shui, D.S. Eggleston, J. Org. Chem. 58 (1993) 7092-7095.
[33] G.V.M. Sharma, Y. Jyothi, P. SreeLakshmi, Synth. Commun. 36 (2006) 2991-3000.
