Nano-SnCl4 ; SiO2: An efficient catalyst for one-pot synthesis of 2,4,5-tri substituted imidazoles under solvent-free conditions

Scientia Iranica

Volumn 20, Issue 3, 2013, Pages 587-591

  Mirjalili, B F ^a   Bamoniri, A ^b   Mirhoseini, M A ^a  

^a YAZD UNIVERSITY   (Iran)

^b UNIVERSITY OF KASHAN   (Iran)

Author keywords

2,4,5 tri substituted imidazoles; Benzil; Heterogeneous catalyst; Solvent free condition

Indexed keywords

CATALYSTS; CHLORINE COMPOUNDS; SILICA;

2,4,5-TRI-SUBSTITUTED IMIDAZOLES; BENZIL; EFFICIENT CATALYSTS; ENVIRONMENTALLY BENIGN; HETEROGENEOUS CATALYST; SOLVENT FREE CONDITIONS; STRUCTURE CHARACTERIZATION; THREE COMPONENT REACTIONS;

TIN COMPOUNDS;

CATALYST; HETEROGENEITY; ORGANIC COMPOUND; OXIDE; SOLVENT;

EID: 84888353018     PISSN: 10263098     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.scient.2013.02.008     Document Type: Article

References (27)

1. Mirjalili, B.F., Bamoniri, A. and Akbari, A. Nano-BF3SiO2: a reusable and eco-friendly catalyst for synthesis of quinoxalines, Chem. Heterocycl. Compd., 47, pp. 487-491 (2011).
2. Sadeghi, B., Mirjalili, B.F. and Hashemi, M.M. BF3SiO2: an efficient reagent system for the one-pot synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles, Tetrahedron Lett., 49, pp. 2575-2577 (2008).
3. Sadeghi, B., Mirjalili, B.F. and Hashemi, M.M. BF3SiO2: an efficient heterogeneous alternative for regio-chemo and stereoselective claisenschmidt condensation, J. Iran. Chem. Soc., 5, pp. 694-698 (2008).
4. Mirjalili, B.F., Bamoniri, A. and Akbari, A. BF3SiO2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo a, j xanthenes, Tetrahedron Lett., 49, pp. 6454-6456 (2008).
5. Pilling, M.J., Gardner, P., Pemble, M.E. and Surman, M. A far-infrared RAIRS investigation of SnCl4 on a silica surface using the buried metal layer approach, Surf. Sci., 418, pp. L1-L7 (1998).
6. Pilling, M.J., Gardner, P., Kausar, R., Pemble, M.E. and Surman, M. A farinfrared RAIRS investigation of SnCl4 and water on thin-film carbon and silica surfaces, Surf. Sci., 433-435, pp. 22-26 (1999).
7. Mirjalili, B.F., Hashemi, M.M., Sadeghi, B. and Emtiazi, H. SnCl4/SiO2: an efficient heterogeneous alternative for one-pot synthesis of - acetamidoketones, J. Chin. Chem. Soc., 56, pp. 386-391 (2009).
8. Li, H.C. and Li, Y.Q. A rapid and convenient synthesis of acylals from aldehydes and acetic anhydrides catalyzed by SnCl4/SiO2, Chin. Chem. Lett., 12, pp. 565-568 (2001).
9. Niknam, K., Zolfigol, M.A., Saberi, D. and Molaee, H. Preparation of silica supported tin chloride: as a recyclable catalyst for the silylation of hydroxyl groups with HMDS, J. Chin. Chem. Soc., 56, pp. 1257-1264 (2009).
10. Lambardino, J.G. and Wiseman, E.H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles, J. Med. Chem., 1(7), pp. 1182-1188 (1974).
11. Jayabharathi, J., Thanikachalam, V., Rajendraprasath, N., Saravanan, K. and Perumal, M.V. Antioxidant potential and antimicrobial screening of some novel imidazole derivatives: greenway efficient one pot synthesis, Med. Chem. Res., 21, pp. 1850-1860 (2012).
12. Welton, T. Solvents for synthesis and catalysis, Chem. Rev., 99, pp. 2071-2084 (1999).
13. Samai, S., Nandi, G.C., Singh, P. and Singh, M.S. L-Proline: an efficient catalyst for the one-pot synthesis of 2, 4, 5-trisubstituted and 1, 2, 4, 5- tetrasubstituted imidazoles, Tetrahedron, 65, pp. 10155-10161 (2009).
14. Teimouri, A. and Najafi Chermahini, A. An efficient and one-pot synthesis of 2, 4, 5-trisubstituted and 1, 2, 4, 5-tetrasubstituted imidazoles catalyzed via solid acid nano-catalyst, J. Mol. Catal. A: Chem., 346, pp. 39-45 (2011).
15. Khosropour, A.R. Ultrasound-promoted greener synthesis of 2, 4, 5- trisubstituted imidazoles catalyzed by Zr(acac)4 under ambient conditions, Ultrason. Sonochem., 15, pp. 659-664 (2008).
16. Xia, M. and Lu, Y. A novel neutral ionic liquid-catalyzed solventfree synthesis of 2, 4, 5-trisubstituted imidazoles under microwave irradiation, J. Mol. Catal. A: Chem., 265, pp. 205-208 (2007).
17. Wolkenberg, S.E., Wisnoski, D.D., Leister, W.H., Wang, Y., Zhao, Z. and Lindsley, C.W. Efficient synthesis of imidazoles from aldehydes and 1, 2-diketones using microwave irradiation, Org. Lett., 6, pp. 1453-1456 (2004).
18. Chary, M.V., Keerthysri, N.C., Vupallapati, S.V.N., Srinivasu, V.N., Lingaiah, N. and Kantevari, S. Tetrabutylammonium bromide (TBAB) in isopropanol: an efficient, novel, neutral and recyclable catalytic system for the synthesis of 2, 4, 5-trisubstituted imidazoles, Catal. Commun., 9, pp. 2013-2017 (2008).
19. Wang, L. and Cai, C. Polymer-supported zinc chloride: a highly active and reusable heterogeneous catalyst for one-pot synthesis of 2, 4, 5- trisubstituted imidazoles, Monatsh. Chem., 140, pp. 541-546 (2009).
20. Joshi, R.S., Mandhane, P.G., Shaikh, M.U., Kale, R.P. and Gill, C.H. Potassium dihydrogen phosphate catalyzed one-pot synthesis of 2, 4, 5-triaryl-1Himidazoles, Chin. Chem. Lett., 21, pp. 429-432 (2010).
21. Jenkins, R. and Snyder, R.L., Introduction to X-Ray Powder Diffractometry, John Wiley & Sons Inc. pp. 89-91 (1996).
22. Shaabani, A., Rahmati, A., Farhangi, E. and Badri, Z. Silica sulfuric acid promoted the one-pot synthesis of trisubstituted imidazoles under conventional heating conditions or using microwave irradiation, Catal. Commun., 8, pp. 1149-1152 (2007).
23. Kidwai, M., Mothsra, P., Bansal, V., Somvanshi, R.K., Ethayathulla, A.S., Dey, S. and Singh, T. One-pot synthesis of highly substituted imidazoles using molecular iodine: a versatile catalyst, J. Mol. Catal. A: Chem., 265, pp. 177-182 (2007).
24. Siddiqui, S.A., Narkhede, U.C., Palimkar, S.S., Daniel, T., Lahoti, R.J. and Srinivasan, K.V. Room temperature ionic liquid promoted improved and rapid synthesis of 2, 4, 5-triaryl imidazoles from aryl aldehydes and 1, 2- diketones or -hydroxyketone, Tetrahedron, 61, pp. 3539-3546 (2005).
25. Sharma, S.D., Hazarika, P. and Konwar, D. An efficient and one-pot synthesis of 2, 4, 5-trisubstituted and 1, 2, 4, 5-tetrasubstituted imidazoles catalyzed by InCl33H2O, Tetrahedron Lett., 49, pp. 2216-2220 (2008).
26. Wang, X.C., Gong, H.P., Quan, Z.J., Li, L. and Ye, H.L. PEG-400 as an efficient reaction medium for the synthesis of 2, 4, 5-triaryl-1H-imidazoles and 1, 2, 4, 5-tetraaryl-1H-imidazoles, Chin. Chem. Lett., 20, pp. 44-47 (2009).
27. Min, L., Wang, Y.H., Tian, H., Yao, Y.F., Shao, J.H. and Liu, B. Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate, J. Fluorine Chem., 127, pp. 1570-1573 (2006).