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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
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Original Articles

One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Using MoO3/SiO2, an Efficient and Recyclable Catalyst

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Pages 762-769 | Received 27 Oct 2009, Published online: 31 Jan 2011

REFERENCES

  • Kumar , P. M. ; Karthikeyan , C. ; Moorthy , N. S. H. N. ; Trivedi , P. Quantitative structure–activity relationships of selective antagonists of glucagon receptor using QuaSAR descriptors . Chem. Pharm. Bull. 2006 , 54 , 1586 – 1591 .
  • Tanigawara , Y. ; Aoyama , N. ; Kita , T. ; Shirakawa , K. ; Komada , F. ; Kasuga , M. ; Okumura , K. CYP2C19 genotype-related efficacy of omerprazole for the treatment of infection caused by Helicobacter Pylori . Clin. Pharmacol. Ther. 1999 , 66 , 528 – 534 .
  • Heers , J. ; Backx , L. J. J. ; Mostmans , J. H. ; Cutsem , V. Antimycotic imidazoles, part 4: Synthesis and antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent . J. Med. Chem. 1979 , 22 , 1003 – 1005 .
  • Lee , J. C. ; Laydon , J. T. ; Mcdonnell , P. C. ; Gallagher , T. F. ; Kumar , S. ; Green , D. ; McNulty , D. ; Blumenthal , M. J. ; Keys , J. R. ; Vatter , S. W. L. ; Strickler , J. E. ; McLaughlin , M. M. ; Siemens , L. R. ; Fisher , S. M. ; Livi , G. P. ; White , J. R. ; Adams , J. L. ; Young , P. R. A protein kinase involved in the regulations of inflammatory cytokine biosynthesis . Nature. 1994 , 372 , 739 – 746 .
  • Blum , C. A. ; Zheng , X. ; Lombaert , S. D. Design, synthesis, and biological evaluation of substituted 2-cyclohexyl-4-phenyl-1H-imidazoles: Potent and selective neuropeptide YY5-receptor antagonists . J. Med. Chem. 2004 , 47 , 2318 – 2325 .
  • Gallagher , T. F. ; Fier-Thompson , S. M. ; Garigipati , R. S. ; Sorenson , M. E. ; Smietana , J. M. ; Lee , D. ; Bender , P. E. ; Lee , J. C. ; Laydon , J. T. ; Griswold , D. E. ; Chabot-Fletcher , M. C. ; Breton , J. J. ; Adams , J. L. 2,4,5-Triarylimidazole inhibitors of IL-1 biosynthesis . Bioorg. Med. Chem. Lett. 1995 , 5 , 1171 – 1176 .
  • Baures , P. W. Heterocyclic HIV-1 protease inhibitors . Org. Lett. 1991 , 2 , 249 – 252 .
  • Cozzi , P. ; Carganico , G. ; Fusar , D. ; Grossoni , M. ; Menichincheri , M. ; Pinciroli , V. ; Tonani , R. ; Vaghi , F. ; Salvati , P. Imidazol-1-yl and pyridin-3-yl derivatives of 4-phenyl-1,2-dihydropyridines combining Ca2+ antagonism and thromboxane A2 synthase inhibition . J. Med. Chem. 1993 , 36 , 2964 – 2972 .
  • Sircar , I. ; Duell , L. B. ; Bristol , A. ; Weisharr , R. E. ; Evans , D. B. Cardiotonic agents 5: 1,2-Dihydro-5-[1H-imidazol-1-yl]-6-methyl-2-oxo-3-pyridinecarbo-nitriles and related compounds: Synthesis and inotropic activity . J. Med. Chem. 1987 , 30 , 1023 – 1029 .
  • Chan , C. ; Bailey , E. J. ; Hartley , C. D. ; Hayman , D. F. ; Huston , J. L. ; Lnglis , G. A. ; Jones , P. S. ; Keeling , S. E. ; Kira , B. E. Inhibitors of cholesterol biosynthesis, 1: 3,5-Dihydroxy-7-(N-imidazolyl)-6-heptenoates and heptanoates, a novel series of 3-hydroxy-3-methylglutarate-CoA reductase inhibitors . J. Med. Chem. 1993 , 36 , 3646 – 3657 .
  • Newman , M. J. ; Rodarte , J. C. ; Benbatoul , K. D. ; Romano , S. J. ; Zhang , C. ; Kranes , S. ; Moran , E. J. ; Uyeda , R. T. ; Dixon , R. ; Guns , E. S. ; Mayer , L. D. Discovery and characterization of OC 144-093, a novel inhibitor of P-glycoprotein-mediated multidrug resistance . Cancer Res. 2000 , 60 , 2964 – 2972 .
  • Heeres , J. ; Backx , L. J. J. ; Mostmans , J. ; Van Cutsem , H. J. Plant growth regulators and therapeutic agents. J. Med. Chem. 1979, 22, 1003–1005.
  • Shaabani , A. ; Rahmati , A. ; Farhangi , E. ; Badri , Z. Silica sulfuric acid promoted the one-pot synthesis of trisubstituted imidazoles under conventional heating conditions or using microwave irradiation . Catl. Commun. 2007 , 8 , 1149 – 1152 .
  • Mohammed , A. F. ; Kokare , N. D. ; Sangshetti , J. N. ; Shinde , D. B. Sulphanilic acid catalyzed facile one-pot synthesis of 2,4,5-triarylimidazoles from benzil/benzoin and aromatic aldehydes . J. Kor Chem. Soc. 2008 , 51 , 418 – 422 .
  • Mohammad , A. A. ; Mivechi , M. ; Kefayati , H. Potassium aluminium sulfate (alum): An efficient catalyst for the one-pot synthesis of trisubstituted imidazoles . Monatsh Chem. 2008 , 139 , 935 – 937 .
  • Liu , J. ; Chen , J. ; Zhao , J. ; Zhao , Y. ; Li , L. ; Zhang , H. A modified procedure for the synthesis of 1-arylimidazoles . Synthesis. 2003 , 2661 – 2666 .
  • Sangshetti , J. N. ; Kokare , N. D. ; Kotharkara , S. A. ; Shinde , D. B. Ceric ammonium nitrate–catalysed three-component one-pot efficient synthesis of 2,4,5-triaryl-1H-imidazoles . J. Chem. Sci. 2008 , 120 , 463 – 467 .
  • Parveen , A. ; Ahmed , M. D. ; Rafi , S. K. ; Shaikh , K. A. ; Deshmukh , S. P. ; Pawar , R. P. Efficient synthesis of 2,4,5-triaryl substituted imidazoles under solvent-free conditions at room temperature . Arkivoc. 2007 , 12 – 18 .
  • Khodaei , M. M. ; Bahrami , K. ; Kavianinia , I. p-TSA-catalyzed synthesis of 2,4,5-triarylimidazoles from ammonium heptamolybdate tetrahydrate in TBAI . J. Chin. Chem. Soc. 2007 , 54 , 829 – 833 .
  • Wang , J. ; Mason , R. ; Derveer , D. V. ; Fena , K. ; Bu , X. R. Convenient preparation of a novel class of imidazo[1,5-a]pyridines: Decisive role by ammonium acetate in chemiselectivity . J. Org. Chem. 2003 , 68 , 5415 – 5418 .
  • Sarshar , S. ; Siev , D. ; Mjalli , M. M. Imidazole libraries on solid support . Tetrahedron Lett. 1996 , 37 , 835 – 838 .
  • Sharma , S. D. ; Hazarika , P. ; Konwar , D. An efficiant and one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3 · 3H2O . Tetrahedron Lett. 2008 , 49 , 2216 – 2220 .
  • Sparks , R. B. ; Combs , A. P. Microwave-assisted synthesis of 2,4,5-triaryl-imidazole: A novel thermally induced N-hydroxy imidazole N‒O bond cleavage . Org. Lett. 2004 , 6 , 2473 – 2475 .
  • Usyatinsky , A. Y. ; Khmelnitsky , Y. L. Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions . Tetrahedron 2000 , 41 , 5031 .
  • 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. 2004 , 6 , 1453 .
  • Dongare , M. K. ; Bhagat , V. V. ; Ramana , C. V. ; Gurjar , M. K. Silica-supported MoO3: A mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar-derived ketoximes . Tetrahedron Lett. 2004 , 45 , 4759 – 4762 .
  • Maurya , S. K. ; Gurjar , M. K. ; Malshe , K. M. ; Patil , P. T. ; Dongare , M. K. ; Kemnitz , E. Solid acid catalyst for fluorotoluene nitration using nitric acid . Green Chem. 2003 , 6 , 720 – 723 .
  • Umbarkar , S. B. ; Biradar , A. V. ; Mathew , S. M. ; Shelke , S. B. ; Malshe , K. M. ; Patil , P. T. ; Dagde , S. P. ; Niphadkar , S. P. ; Dongare , M. K. Vapor phase nitration of benzene using mesoporous MoO3/SiO2 solid acid catalyst . Green Chem. 2006 , 8 , 488 – 493 .
  • Weiss , M. ; Abbel , M. The catalytic oxidation of benzoin to benzil . J. Am. Chem. Soc. 1948 , 70 , 3666 – 3667 .
  • McKillop , A. ; Swann , B. ; Ford , M. E. ; Taylor , E. C. Thallium in organic synthesis, XXXVIII: Oxidation of chalcones, deoxybenzoins, and benzoins with thallium(III) nitrate (TTN). J. Am. Chem. Soc. 1973, 95, 3641–3645.
  • Zhang , G. S. ; Shi , Q. Z. ; Chen , M. F. ; Cai , K. Ammonium chlorochromate adsorbed on alumina: A new reagent for the oxidation of alcohols and benzoins to the corresponding carbonyl compounds . Synth. Commun. 1997 , 27 , 953 – 956 .
  • Chary , M. V. ; Keerthysri , N. C. ; Vupallapati , S. V. N. ; Lingaiah , N. ; Kantevari , S. Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral, and recyclable catalyst system for the synthesis of 2,4,5-trisubstituted imidazoles . Catal. Comm. 2008 , 9 , 2013 – 2017 .

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