Synthesis, Characterization of Highly Efficient SO42-/ CeO2–ZrO2 Solid Acid Catalyst and Activity Studies of 2, 4, 5-triaryl imidazoles
Author Affiliations
- 1Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad Sub-Campus, Osmanabad, MS, INDIA
Res.J.chem.sci., Volume 4, Issue (7), Pages 18-23, July,18 (2014)
Abstract
SO/ CeO2ZrO2 solid acid catalyst has been synthesized by coprecipitation followed by impregnation method. Zirconyl oxychloride and ceric ammonium nitrate is used as zirconia and ceria precursor respectively, ammonia is used as precipitating agent and chlorosulfonic acid is used as sulphating agent. The structure characterization of this solid acid catalyst has been studied by FT-IR, XRD, and TGA-DSC. Synthesized solid acid catalyst is employ for preparation of 2,4,5-trisubstituted imidazoles via three-component reactions of benzoin, aldehydes and ammonium acetate under mild conditions.The desired products were formed in high to moderate yields.
References
- Khabibullina G. R., Akhmetova V.R., Abdullin M. F.,Tyumkina T. V., Khalilov L. M., Ibragimov, A. G.,Dzhemilev U. M., Multicomponent reactions of amino alcohols with CH2O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles, Tetrahedron, 70,3502-3509 (2014)
- Gorea R.P., Rajput A.P., A review on recent progress in multicomponent reactions of pyrimidine synthesis., Drug Invention Today,5, 148-152 (2013)
- Liu Y.-p., Liu J.-m., Wang X., ChengT.-m, Li R.-t., Multicomponent reactions leading to symmetric and asymmetric multi-substituted 1,4-dihydropyridines on montmorillonite, Tetrahedron, 69, 5242-5247 (2013)
- Reddy B. M., Thirupathi B., Patil M. K., Highly efficient promoted zirconia solid acid catalysts for synthesis of aminonitriles using trimethylsilyl cyanide, J. Mol. Catal. A: Chem., 307, 154–159 (2009)
- Reddy B. M., Patil M. K., Reddy B. T., An Efficient and Ecofriendly WO–ZrOSolid Acid Catalyst for Classical Mannich Reaction, Catal. Lett.,125, 97–103 (2008)
- Wolkenberg S.E., Wisnoski D.D., Leister W.H., Wang Y., Zhao Z., Lindsley C.W., Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation, Org. Lett. 6, 1453–1456 (2004)
- Xia M., 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, 205–208,(2007)
- Chary M.V., Keerthysri N.C., Vupallapati S.V.N., Srinivasu V.N., Lingaiah N. ,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.,, 2013–2017,(2008)
- Khosropour A.R., Ultrasound-promoted greener synthesis of 2, 4, 5-trisubstituted imidazoles catalyzed by Zr(acac)under ambient conditions, Ultrason. Sonochem., 15, 659–664,(2008)
- Wang L., 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, 541–546 (2009)
- Samai S., Nandi G.C., Singh P., 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, 10155–10161 (2009)
- Zang H., Su Q.; Mo Y., Cheng B.W. , Jun S., Ionic liquid[EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles, Ultrason. Sonochem.,17, 749–751,(2010)
- Joshi R.S., Mandhane P.G., Shaikh M.U., Kale R.P. , Gill C.H., Potassium dihydrogen phosphate catalyzed one-pot synthesis of 2, 4, 5-triaryl-1Himidazoles, Chin. Chem. Lett.,21, 429–432 (2010)
- Teimouri A. , Najafi Chermahini A., An efficient and onepot synthesis of 2, 4, 5-trisubstituted and 1, 2, 4, 5- tetrasubstituted imidazoles catalyzed via solid acid nanocatalyst, J. Mol. Catal. A: Chem., 346, 39–45, (2011)
- Khadijeh H., Hossein B., Oskooie A., Taheri S., Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2·6H2O underheterogeneous system, Majid M. J. Mol. Catal. A: Chem., 263, 279–281 (2007)
- Safari J., Naseh S., Zarnegar Z.; Akbari Z., Applications of microwave technology to rapid synthesis of substituted imidazoles on silica-supported SbCl3 as an efficient heterogeneous catalyst, Journal of Taibah University for Science, Available online 20 February 2014, In Press,
- Lambardino J.G., Wiseman E.H., Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles, J. Med. Chem., 17, 1182-1188 (1974)
- Puratchikody A., Doble M. Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4,5-diphenyl-1H-imidazoles, Bioorg. Med.Chem. Lett., 15, 1083-1090 (2007)
- Wauquier A. , Van Den Broeck W.A.E. ,Verheyen J.L. Janssen P.A.J., Electroencephalographic study of the short-acting hypnotics etomidate and methohexital in dogs, Eur. J. Pharmacol., 47, 367-377 (1978)
- Tanigawara Y., Aoyama N., Kita T., Shirakawa K., Komada F., Kasuga M., Okumura K., CYP2C19 genotype–related efficacy of omeprazole for the treatment of infection caused by Helicobacter pylori, Clin. Pharmacol. Ther., 66, 528-534 (1999)
- Heers J. , Backx L.J.J., Mostmans J.H. , Van Cutsem J., Antimycotic imidazoles. Part 4. Synthesis and antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent, J. Med. Chem., 22, 1003-1005 (1979)
- Hunkeler W., Mohler H., Pieri L., Polc, P., Bonetti E.P., Cumin R., Schaffner R., Haefely W,. Selective antagonists of benzodiazepines, Nature, 290, 514-516,(1981)
- Zhai Y., Zhang H., Hu J., Yi B. Preparation and characterization of sulfated zirconia (SO2/ZrO)/Nafion composite membranes for PEMFC operation at high temperature/low humidity, J. Memb. Sci.,208, 148–155,(2006)
- Yamaguchi T., Jin, T. , Tanabe K., Structure of acid sites on sulfur-promoted iron Oxide, J. Phys. Chem., 90, 3148–3152 (1986)
- Shelke K.F., Sapkal S.B., Sonar S.S., Madje B. R., Shingate B. B., Shingare. M. S., An Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazole Derivatives Catalyzed by Boric Acidin Aqueous Media Under Ultrasound-Irradiation, Bull. Korean Chem. Soc. 30, 5-20 (2009)
- Mohammadi A.A , Mivechi M., Kefayati H., Potassium aluminum sulphate (alum): an efficient catalyst for the one-pot synthesis of trisubstituted Midazoles, Monatsh Chem.,139, 935-937 (2008)