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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 16
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Original Articles

Three-Component, One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Catalyzed by TiCl4-SiO2 Under Conventional Heating Conditions or Microwave Irradiation

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Pages 2359-2373 | Received 26 Feb 2010, Published online: 14 Jun 2011

REFERENCES

  • Domling , A. Isocyanide based multicomponent reactions in combinatorial chemistry . Comb. Chem. High Throughput Screening 1998 , 1 , 1 – 22 .
  • Ugi , I. ; Domling , A. ; Gruber , B. ; Almstetter , M. Multicomponent reactions and their libraries—a new approach to preparative organic chemistry . Croat. Chem. Acta. 1997 , 70 , 631 – 647 .
  • Armstrong , R. ; Combs , A. ; Tempest , P. ; Brown , D. ; Keating , T. Multiple-component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. 1996 , 29 , 123 – 131 .
  • Nicolaou , K. C. ; Montagnon , T. ; Snyder , S. A. Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis. Chem. Commun. 2003, 551–565.
  • Wasilke , J. C. ; Obrey , S. J. ; Baker , R. T. ; Bazan , G. C. Concurrent tandem catalysis . Chem. Rev. 2005 , 105 , 1001 – 1020 .
  • Ramon , D. J. ; Yus , M. Asymmetric multicomponent reactions (AMCRs): The new frontier . Angew. Chem. 2005 , 44 , 1602 – 1634 .
  • Tietze , L. F. Domino reactions in organic synthesis . Chem. Rev. 1996 , 96 , 115 – 136 .
  • Tietze , L. F. ; Haunert , F. In stimulating concepts in chemistry ; F. Vogtle , J. F. Stoddart , M. Shibasaki , (Eds.); Wiley-VCH : Weinheim , 2000 ; p. 39 .
  • Tietze , L. F. ; Modi , A. Multicomponent domino reactions for the synthesis of biologically active natural products and drugs . Med. Res. Rev. 2000 , 20 , 304 – 322 .
  • Lombardino , J. G. ; Wiseman , E. H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles . J. Med. Chem. 1974 , 17 , 1182 – 1188 .
  • Mjalli , A. M. M. ; Sarshar , S. 1,2,4,5-Tetrasubstituted imidazoles as modulators of multi-drug resistance . U.S. Patent 570082619, 1997 .
  • Grimmett , M. R. In A. R. Katrizky , C. W. Rees , (Eds.); Comprehensive Heterocyclic Chemistry ; Pergamon Press : London , vol. 5 , 1984 , p. 374 .
  • Laufer , S. A. ; Zimmermann , W. ; Ruff , K. J. Tetrasubstituted imidazole inhibitors of -cytokine release: Probing substituents in the N-1 position . J. Med. Chem. 2004 , 47 , 6311 – 6325 .
  • Kantevari , S. ; Nair , C. K. S. ; Pardhasaradhi , M. A practical synthesis of 5-(4′-methylbiphenyl-2-yl)-1H-tetrazole . J. Heterocycl. Chem. 2006 , 43 , 1353 – 1356 .
  • 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 – 1456 .
  • Maier , T. ; Schmierer , R. ; Bauer , K. ; Bieringer , H. ; Buerstell , H. ; Sachse , B. 1-Substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides. U.S. Patent 4820335, 1989 .
  • Wang , L. ; Woods , K. W. ; Li , Q. ; Barr , K. J. ; McCroskey , R. W. ; Hannick , S. M. ; Gherke , L. ; Credo , R. B. ; Hui , Y. H. ; Marsh , K. ; Warner , R. ; Lee , J. Y. ; Zielinsky-Mozng , N. ; Frost , D. ; Rosenberg , S. H. ; Sham , H. L. Potent, orally active heterocycle-based combretastatin A-4 analogues: Synthesis, structure–activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation . J. Med. Chem. 2002 , 45 , 1697 – 1711 .
  • Lombardino , J. G. Anti-inflammatory imidazole. DE Patent 2155558, 1972. U.S. 3772441, 1973 .
  • Black , J. W. ; Durant , G. J. ; Emmett , J. C. ; Ganellin , C. R. Sulphur-methylene isosterism in the development of metiamide, a new histamine H2-receptor antagonist . Nature 1974 , 248 , 65 – 67 .
  • Ucucu , U. ; Karaburun , N. G. ; Iskdag , I. Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives . Farmaco 2001 , 56 , 285 – 290 .
  • Khan , M. S. ; Siddiqui , S. A. ; Siddiqui , M. S. R. ; Goswami , U. ; Srinivasan , K. V. ; Khan , M. I. Antibacterial activity of synthesized 2,4,5-trisubstituted imidazole derivatives . Chem. Biol. Drug. Des. 2008 , 72 , 197 – 204 .
  • Chang , L. L. ; Sidler , K. L. ; Cascieri , M. A. ; Laszlo , S. D. ; Koch , G. ; Li , B. ; MacCoss , M. ; Mantlo , N. ; O'Keefe , S. ; Pang , M. ; Rolando , A. ; Hagmann , W. K. Substituted imidazoles as glucagon receptor antagonists . Bioorg. Med. Chem. Lett. 2001 , 11 , 2549 – 2553 .
  • 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 , I. R. ; Fisher , S. M. ; Livi , G. P. ; White , J. R. ; Adams , J. L. ; Young , P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994 , 372 , 739 – 746 .
  • Takle , A. K. ; Brown , M. J. B. ; Davies , S. ; Dean , D. K. ; Francis , G. ; Gaiba , A. ; Hird , A. W. ; King , F. D. ; Lovell , P. J. ; Naylor , A. ; Reith , A. D. ; Steadman , J. G. ; Wilson , D. M. The identification of potent and selective imidazole-based inhibitors of B-Raf kinase. Bioorg. Med. Chem. Lett. 2006, 16, 378–381.
  • Khanna , I. K. ; Weier , R. M. ; Yu , Y. ; Xu , X. D. ; Koszyk , F. J. ; Collins , P. W. ; Koboldt , C. M. ; Veenhuizen , A. W. ; Perkins , W. E. ; Casler , J. J. ; Masferrer , J. L. ; Zhang , Y. Y. ; Gregory , S. A. ; Seibert , K. ; Isakson , P. C. 1,2-Diarylimidazoles as potent, cyclooxygenase-2 selective, and orally active antiinflammatory agents . J. Med. Chem. 1997 , 40 , 1634 – 1647 .
  • Lange , J. H. M. ; Van Stuivenberg , H. H. ; Coolen , H. K. A. C. ; Adolfs , T. J. P. ; McCreary , A. C. ; Keizer , H. G. ; Wals , H. C. ; Veerman , W. ; Borst , A. J. M. ; de Looff , W. ; Verveer , P. C. ; Kruse , C. G. Bioisosteric replacements of the pyrazole moiety of rimonabant: synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antagonists . J. Med. Chem. 2005 , 48 , 1823 – 1838 .
  • Gallagher , T. H. ; 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 .
  • Lantos , I. ; Zhang , W. Y. ; Shui , Y. ; Eggleston , D. S. Synthesis of imidazoles via hetero-Cope rearrangements . J. Org. Chem. 1993 , 58 , 7092 – 7095 .
  • Zhang , C. ; Moran , E. J. ; Woiwade , T. F. ; Short , K. M. ; Mjalli , A. M. M. Synthesis of tetrasubstituted imidazoles via α-(N-acyl-N-alkylamino)-β-ketoamides on Wang resin . Tetrahedron Lett. 1996 , 37 , 751 – 754 .
  • Zaman , S. ; Mitsuru , K. ; Abell , A. D. Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: Application to amino acid mimetics with a C-terminal imidazole . Org. Lett. 2005 , 7 , 609 – 611 .
  • Bleicher , K. H. ; Gerber , F. ; Wuthrich , Y. ; Alanine , A. ; Capretta , A. Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols . Tetrahedron Lett. 2002 , 43 , 7687 – 7690 .
  • Khosropour , A. R. Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim]HSO4 as a powerful Brønsted acidic ionic liquid . Can. J. Chem. 2008 , 86 , 264 – 269 .
  • Chary , M. V. ; Keerthysri , N. C. ; Vupallapati , S. ; 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. 2008 , 9 , 2013 – 2017 .
  • Shaabani , A. ; Rahmati , A. ; Aghaaliakbari , B. ; Safaei-Ghomi , J. 1,1,3,3-N,N,N′,N′-Tetramethylguanidinium trifluoroacetate ionic liquid–promoted efficient one-pot synthesis of trisubstituted imidazoles . Synth. Commun. 2006 , 36 , 65 – 70 .
  • Siddiqui , S. A. ; Narkhede , U. C. ; Palimkar , S. S. ; Daniel , T. ; Lahoti , R. J. ; 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 α -hydroxyketone . Tetrahedron 2005 , 61 , 3539 – 3546 .
  • Xia , M. ; Lu , Y. A novel neutral ionic liquid–catalyzed solvent-free synthesis of 2,4,5-trisubstituted imidazoles under microwave irradiation . J. Mol. Catal. A: Chem. 2007 , 265 , 205 – 208 .
  • Heravi , M. M. ; Bakhtiari , K. ; Oskooie , H. A. ; Taheri , S. Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2 · 6H2O under heterogeneous system . J. Mol. Catal. A: Chem. 2007 , 263 , 279 – 281 .
  • Sharma , G. V. M. ; Jyothi , Y. ; Sree Lakshmi , P. Efficient room-temperature synthesis of tri- and tetrasubstituted imidazoles catalyzed by ZrCl4 . Synth. Commun. 2006 , 36 , 2991 – 3000 .
  • Kidwai , M. ; Mothsra , P. ; Bansal , V. ; Somvanshi , R. K. ; Ethayathulla , A. S. ; Dey , S. ; Singh , T. P. One-pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst. J. Mol. Catal. A: Chem. 2007, 265, 177–182.
  • Wang , L. ; Wang , Y. ; Tian , H. ; Yao , Y. ; Shao , J. ; 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. 2006 , 127 , 1570 – 1573 .
  • Shen , M. ; Cai , C. ; Yi , W. Ytterbium perfluorooctanesulfonate as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles . J. Fluorine Chem. 2008 , 129 , 541 – 544 .
  • Sharma , S. D. ; Hazarika , P. ; Konwar , D. An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3 · 3H2O . Tetrahedron Lett. 2008 , 49 , 2216 – 2220 .
  • Jadhave , S. D. ; Kokare , N. D. ; Jadhave , S. D. Phosphomolybdic acid catalyzed facile one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil and aromatic aldehydes . J. Heterocycl. Chem. 2009 , 45 , 1461 – 1464 .
  • 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 .
  • 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 acid in aqueous media under ultrasound irradiation . Bull. Korean Chem. Soc. 2009 , 30 , 1057 – 1060 .
  • Kokare , N. D. ; Sangshetti , J. N. ; Shinde , D. B. One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-triaryl-1H-imidazoles using oxalic acid catalyst . Synthesis 2007 , 2829 – 2834 .
  • 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 .
  • Shaabani , A. ; Maleki , A. ; Behnam , M. Tandem oxidation process using ceric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions . Synth. Commun. 2009 , 39 , 102 – 110 .
  • 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 2009 , 65 , 10155 – 10161 .
  • Sangshetti , J. N. ; Shinde , D. B. ; Kokare , N. D. ; Kotharkar , S. A. Sodium Bisulfite as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil or benzoin and aromatic aldehydes . Monatsh. Chem. 2008 , 139 , 125 – 127 .
  • Wang , X. C. ; Gong , H. P. ; Quan , Z. J. ; Li , L. ; 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. 2009 , 20 , 44 – 47 .
  • 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. 2009 , 140 , 541 – 546 .
  • Gadekar , L. S. ; Mane , S. R. ; Arbad , B. R. ; Katkar , S. S. ; Lande , M. K. Scolecite as an efficient heterogeneous catalyst for the synthesis of 2,4,5-triarylimidazoles . Cent. Eur. J. Chem. 2009 , 7 , 550 – 554 .
  • Karimi , A. R. ; Alimohammadi , Z. ; Amini , M. M. Wells–Dawson heteropolyacid supported on silica: A highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles . Mol. Divers. 2010 , 14 , 635 – 641 .
  • Xie , T. ; McAuley , K. B. ; Hsu , J. C. ; Bacon , D. W. Gas phase ethylene polymerization: Production processes, polymer properties, and reactor modeling. Ind. Eng. Chem. Res. 1994, 33, 449–479.
  • Sobota , P. ; Szafert , S. Ionization of TiCl4 and MgCl2 during the formation of a high-activity α-olefin polymerization catalyst: Crystal structures of [cis-{C2H4(CO2Et)2}2Cl2Ti][SbCl6]2 · CH2Cl2 and [Mg{C2H4(CO2Et)2}3][MgCl4] · 2CH2Cl2 . Inorg. Chem. 1996 , 35 , 1778 – 1781 .
  • Haukka , S. ; Lakomaa , E. L. ; Root , A. An IR and NMR study of the chemisorption of titanium tetrachloride on silica . J. Phys. Chem. 1993 , 97 , 5085 – 5094 .
  • Damianov , D. ; Velikova , M. ; Ivanov , I. ; Vlaev , L. On the mechanism of interaction between TiCl4 vapour and surface OH groups of amorphous SiO2 . J. Non-cryst. Solids 1988 , 105 , 107 – 113 .
  • Varma , R. S. Solvent-free organic syntheses using supported reagents and microwave irradiation . Green Chem. 1999 , 43 – 54 .

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