363
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

MCM-41 Mesoporous Silica: Efficient and Reusable Catalyst for the Synthesis of 2,4,5-Trisubstituted Imidazoles Under Solvent-Free Conditions

, &
Pages 1310-1314 | Received 15 Sep 2010, Accepted 26 Jul 2011, Published online: 02 Dec 2011

REFERENCES

  • Lombardino , J. G. and Wiseman , E. H. 1974 . Preparation and anti-inflammatory activity of some nonacidic trisubstituted imidazoles . J. Med. Chem. , 17 : 1182 – 1188 .
  • Cui , B. , Zheng , B. L. , He , K. and Zheng , Q. Y. 2003 . Imidazole alkaloids from Lepidium meyenii . J. Nat. Prod. , 66 : 1101 – 1103 .
  • Abrahams , S. L. , Hazen , R. J. , Batson , A. G. and Phillips , A. P. 1989 . A chemically novel platelet aggregation inhibitor . J. Pharmacol. Exp. Ther. , 249 : 359 – 365 .
  • Wasserscheid , P. and Keim , W. 2000 . Ionic liquids: New solutions for transition metal catalysis . Angew. Chem. Int. Ed. Eng. , 39 : 37872 – 37877 .
  • Nagawade , R. R. and Shinde , D. B. 2007 . Zirconyl (IV) chloride-catalyzed multicomponent reaction of β-naphthols . Acta Chim. Slov. , 54 : 642 – 646 .
  • Oskooie , H. A. , Alimohammadi , Z. and Heravi , M. M. 2006 . Microwave-assisted solid-phase synthesis of 2,4,5-triaryl imidazoles in solventless system: An improved protocol . Heterotom. Chem. , 17 : 699 – 702 .
  • Wang , J. , Mason , R. , Derveer , D. V. , Feng , K. and Bu , X. R. 2003 . Convenient preparation of a novel class of imidazo[1,5-a]pyridines: Decisive role by ammonium acetate in chemoselectivity . J. Org. Chem. , 68 : 5415 – 5418 .
  • Shaabani , A. and Rahmati , A. 2006 . Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles . J. Mol. Catal. A Chem. , 249 : 246 – 248 .
  • Heravi , M. M. , Bakhtiari , K. , Oskooie , H. A. and Taheri , S. 2007 . Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2·6H2O under heterogeneous system . J. Mol. Catal. A Chem. , 263 : 279 – 281 .
  • Sharma , G. V.M. , Jyothi , Y. and Lakshmi , P. S. 2006 . Efficient room-temperature synthesis of tri- and tetrasubstituted imidazoles catalyzed by ZrCl4 . Synth. Commun. , 36 : 2991 – 3000 .
  • Siddiqui , S. A. , Narkhede , U. C. , Palimkar , S. S. , Daniel , T. , Lahoti , R. J. and Srinivasan , K. V. 2005 . Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triaryl imidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketone . Tetrahedron , 61 : 3539 – 3546 .
  • Sangshetti , J. N. , Kokare , N. D. , Kotharkara , S. A. and Shinde , D. B. 2008 . Ceric ammonium nitrate catalysed three component one-pot efficient synthesis of 2,4,5-triaryl-1H-imidazoles . J. Chem. Sci. , 5 : 463 – 467 .
  • Beck , J. S. , Vartuli , J. C. , Roth , W. J. , Leonowicz , M. E. , Kresge , C. T. , Schmitt , K. D. , Chu , C. T. , Olson , D. H. , Sheppard , E. V. , McCullen , S. B. , Higgins , J. B. and Schlenker , J. L. 1992 . A new family of mesoporous molecular sieves prepared with liquid crystal templates . J. Am. Chem. Soc. , 114 : 10834 – 10843 .
  • Heravi , M. M. , Rahimzadeh , M. , Bakavoli , M. and Ghassemzadeh , M. 2004 . Pd-Cu catalyzed heterocyclization during Sonogashira coupling: Synthesis of 3-benzylthiazolo[3,2-a]benzimidazole . Tetrahedron Lett. , 45 : 5747 – 5749 .
  • Heravi , M. M. , Rahimzadeh , M. , Bakavoli , M. and Ghassemzadeh , M. 2005 . Regioselective synthesis of 6-benzylthiazolo[3,2-b]1,2,4-triazoles during Sonogashira coupling . Tetrahedron Lett. , 46 : 1607 – 1610 .
  • Malakooti , R. , Farzaneh , F. and Ghandi , M. 2006 . Synthesis, characterization and studies on catalytic behavior of Mn(II) complex with 2,2′-bipyridine 1,1′-dioxide ligand within nanoreactors of MCM-41 . J. Sci.; I. R. I. , 17 : 43 – 52 .
  • Wang , J. A. , Chen , L. F. , Norena , L. E. and Navarrete , J . 2009 . Spectroscopic study and catalytic evaluation of mesostructured Al-MCM-41 and Pt/H3PW12O40/Al-MCM-41 catalysts . J. Appl. Catal. A Gen. , 357 : 223 – 235 .
  • Samai , S. , Nandi , G. Ch. , Singh , P. and Singh , M. S. 2009 . 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 .
  • Uchida , H. , Shimizu , T. , Reddy , P. Y. , Nakamura , S. H. and Toru , T. 2003 . Solvent-free efficient synthesis of 2,4,5-triarylimidazolines from aromatic aldehydes and hexamethyldisilazane . Synthesis , 8 : 1236 – 1240 .
  • Coraore , G. R. , Cescon , L. A. , Dessauer , R. , Silversmith , E. F. and Urban , E. J . 1971 . Properties of triarylimidazolyl radicals and their dimers . J. Org. Chem. , 36 : 2262 – 2267 .
  • Dauwe , C. and Buddrus , J . 1995 . Synthesis of enantiopure C2-chiral amidines . Synthesis , 2 : 171 – 172 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.