One-pot synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles promoted by nano-TiCl4.SiO2

Scientia Iranica

Volumn 19, Issue 3, 2012, Pages 565-568

  Mirjalili, B F ^a   Bamoniri, A H ^b   Zamani, L ^a  

^a YAZD UNIVERSITY   (Iran)

^b UNIVERSITY OF KASHAN   (Iran)

Author keywords

1, 2, 4, 5 tetrasubstituted imidazoles; Benzil; One pot synthesis; Solvent free condition; Supported Lewis acid

Indexed keywords

NATURAL SCIENCES;

1, 2, 4, 5-TETRASUBSTITUTED IMIDAZOLES; BENZIL; ONE-POT SYNTHESIS; SOLVENT FREE CONDITIONS; SUPPORTED LEWIS ACID;

ENGINEERING;

CATALYST; NANOTECHNOLOGY;

EID: 84863705381     PISSN: 10263098     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.scient.2011.12.013     Document Type: Article

References (28)

1. S.A. Laufer, W. Zimmermann, and K.J. Ruff Tetrasubstituted imidazole inhibitors of cytokine release: probing substituents in the N - 1 position J. Med. Chem. 47 2004 6311 6325
2. M. Misono Unique acid catalysis of heteropoly compounds (heteropolyoxometalates) in the solid state Chem. Commun. 2001 1141 1152
3. 2-receptor antagonist Nature 248 1974 65 67
4. U. Ucucu, N.G. Karaburun, and I. Iskdag Synthesis and analgesic activity of some 1-benzyl-2-substituted-4, 5-diphenyl-1H-imidazole derivatives Il Farmaco. 56 2001 285 290
5. J.A. Murry Syntheticmethodology utilized to prepare substituted imidazole p38MAPkinase inhibitors.CurrOpin Drug Discov. Dev. 6 2003 945 965
6. S.E. de Laszlo, C. Hacker, B. Li, D. Kim, M. MacCoss, N. Mantlo, J.V. Pivnichny, L. Colwell, G.E. Koch, M.A. Cascieri, and W.K. Hagmann Potent, orally absorbed glucagon receptor antagonists Bioorg. Med. Chem. Lett. 9 1999 641 646
7. P.A. Eyers, M. Craxton, N. Morrice, P. Cohen, and M. Goedert Conversion of SB 203580-insensitive MAP kinase family members to drug-sensitive forms by a single amino-acid substitution Chem. Biol. 5 1998 321 328
8. M.J. Newman, J.C. Rodarte, K.D. Benbatoul, S.J. Romano, C. Zhang, S. Krane, E.J. Moran, R.T. Uyeda, R. Dixon, E.S. Guns, and L.D. Mayer Discovery and characterization of OC144-093, a novel inhibitor of P-glycoprotein-mediated multidrug resistance Cancer Res. 60 2000 2964 2972
9. M. Antolini, A. Bozzoli, C. Ghiron, G. Kennedy, T. Rossi, and A. Ursini Analogues of 4, 5-bis(3, 5-dichlorophenyl)-2-trifluoromethyl-1H-idazole as potential antibacterial agents Bioorg. Med. Chem. Lett. 9 1999 1023 1028
10. L. Wang, K.W. Woods, Q. Li, K.J. Barr, R.W. McCroskey, S.M. Hannick, L. Gherke, R.B. Credo, Y-H. Hui, K. Marsh, R. Warner, J.Y. Lee, N. Zielinsky-Mozng, D. Frost, S.H. Rosenberg, and H.L. Sham Potent, orally active heterocycle-based combretastatin α-4 analogues: synthesis, structure-activity relationship, pharmacoki-netics, and in vivo antitumor activity evaluation J. Med. Chem. 45 2001 1697 1711
11. S. Balalaei, and A. Arabanian One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation Green Chem. 2 2000 274 276
12. 4 support Catal. Commun. 7 2006 728 732
13. M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey, and T.P. Singh One-pot synthesis of highly substituted imidazoles using molecular iodine: a versatile catalyst J. Mol. Catal. A: Chem. 265 2007 177 182
14. 2O): a mild and efficient reusable catalyst for the one-pot synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles under conventional heating and microwave irradiation J. Mol. Catal. A: Chem. 266 2007 104 108
15. M.M. Heravi, F. Derikvand, and F.F. Bamoharram Highly efficient, four-component one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts J. Mol. Catal. A: Chem. 263 2007 112 114
16. S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, and L. Nagarapu Synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N-sulfamic acid as a recyclable solid acid catalyst J. Mol. Catal. A: Chem. 266 2007 109 113
17. 2O Tetrahedron Lett. 49 2008 2216 2220
18. 4 Synth. Commun. 36 2006 2991 3000
19. 2 an efficient reagent system for the one-pot synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles Tetrahedron Lett. 49 2008 2575 2577
20. S.N. Murthy, B. Madhav, and Y.V.D. Nageswar DABCO as a mild and efficient catalytic system for the synthesis of highly substituted imidazoles via multi-component condensation strategy Tetrahedron Lett. 51 2010 5252 5257
21. X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, and H.L. Ye 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 Chinese Chem. Lett. 20 2009 44 47
22. K. Niknam, A. Deris, F. Naeimi, and F. Majleci Synthesis of 1,2,4,5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N-sulfamic acid as a recyclable solid acid catalyst Tetrahedron Lett. 52 2011 4642 4645
23. J.L.D. Souza, F. Fabri, R. Buffon, and R. Schuchardet Reduced anatase on silica as a support for a Ziegler catalyst Appl. Catal. A. Gen. 323 2007 234
24. 2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo [ a, j ] xanthenes Tetrahedron Lett. 49 2008 6454 6456
25. 2: an efficient heterogeneous iternative for regio-chemo and stereoselective claisn-schmidt condensation J. Iran. Chem. Soc. 8 2011 694 698
26. 2 J. Iran. Chem. Soc. 8 2011 S135 S140
27. V.A. Zettler, and C.A. Brown Infrared spectra of some Ti-O-Si, Ti-O-Ti and Si-O-Si compounds J. Am. Chem. Soc. 79 1957 1174 1178
28. 4-modified by means of quantitative surface analysis Phys. Chem. Chem. Phys. 1 2008 2569 2572