195
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

ONE-POT SYNTHESIS OF 2,4,5-TRISUBSTITUTED IMIDAZOLES USING [BPy]H2PO4, AN EFFICIENT AND RECYCLABLE CATALYST

&
Pages 189-196 | Published online: 10 Jan 2013

REFERENCES

  • Wasserscheid , P. ; Keim , W. Ionic Liquids—New “Solutions” for Transition Metal Catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3772 – 3789 .
  • Heeres , J. ; Backx , L.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. 1979, 22, 1003–1005.
  • 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. 1999 , 66 , 528 – 534 .
  • Brimblecombe , R.W. ; Duncan , W.A.M. ; Durant , G.J. ; Emmett , J.C. ; Ganellin , C.R. ; Parons , M.E. Cimetidine Nonthiourea Histamine H2-Receptor Antagonist . J. Int. Med. Res. 1975 , 3 , 86 – 92 .
  • 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. 1978 , 47 , 367 – 377 .
  • Shelke , K.F. ; Sapkal , S.B. ; Kakade , G.K. ; Shingate , B.B. ; Shingare , M.S. Cellulose Sulfuric Acid as a Bio-Supported and Recyclable Solid Acid Catalyst for the One-Pot Synthesis of 2,4,5-Triarylimidazoles Under Microwave Irradiation . Green Chem. Lett. Rev. 2010 , 3 , 27 – 32 .
  • 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 .
  • Wang , L.W. ; Wang , Y.H. ; Tian , H. ; Yao , Y.F. ; Shao , J.H. ; 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 .
  • Mohammadi , A.A. ; Mivechi , M. ; Kefayati , H. Potassium Aluminum Sulfate (Alum): An Efficient Catalyst for the One-Pot Synthesis of Trisubstituted Imidazoles . Monatsh. Chem. 2008 , 139 , 935 – 937 .
  • Sangshetti , J.N. ; Kokare , N.D. ; Kotharkar , S.A. ; Shinde , D.B. ZrOC12 · 8H2O Catalyzed One-Pot Synthesis of 2,4,5-Triaryl-1H-Imidazoles and Substituted 1,4-Di(4,5-diphenylimidazolyl) Benzene . Chin. Chem. Lett. 2008 , 19 , 762 – 766 .
  • 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 .
  • Shitole , N.V. ; Shelke , K.F. ; Sonar , S.S. ; Sadaphal , S.A. ; Shingate , B.B. ; Shingare , M.S. L-Proline as an Efficient Catalyst for the Synthesis of 2,4,5-Triaryl-1H-imidazoles . Bull. Korean Chem. Soc. 2009 , 30 , 1963 – 1966 .
  • Wolkenberg , S.E. ; Winoski , 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 .
  • Dutta , S. Synthesis and Anthelmintic Activity of Some Novel 2-Substituted 4,5-Diphenyl Imidazoles . Acta Pharm. 2010 , 60 , 229 – 235 .
  • Eseola , A.O. ; Sun , W. ; Li , W. ; Woods, J.A.O. Syntheses of New Imidazole Ligand Series and Evaluation of 1-,2- and 4,5-Imidazole Substituent Electronic and Steric Effects on N-Donor Strengths . J. Mol. Struct. 2010 , 984 , 117 – 124 .
  • Shelke , K. ; Kakade , G. ; Shingate , B. ; Shingare , M. Microwave-Induced One-Pot Synthesis of 2,4,5-Triarylimidazoles Using Glyoxylic Acid as a Catalyst Under Solvent-Free Conditions . Rasayan J. Chem. 2008 , 1 , 489 – 494 .
  • Sangshetti , J.N. ; Kokare , N.D. ; Kothakar , S.A. ; Shinde , D.B. 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 .
  • Satyanarayana , V.S.V. ; Sivakumar , A. An Efficient and Novel One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles Catalyzed by UO2(NO3)2 · 6H2O Under Heterogeneous Conditions . Chem. Pap. 2011 , 65 , 519 – 526 .
  • Bhosale , S.V. ; Kalyankar , M.B. ; Nalage , S.V. ; Bhosale , D.S. ; Pandhare , S.L. ; Kotbagi , T.V. ; Umbarkar , S.B. ; Dongare , M.K. One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Using MoO3/SiO2, an Efficient and Recyclable Catalyst . Synth. Commun. 2011 , 41 , 762 – 769 .
  • 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 .
  • Siddiqui , S.A. ; Narkhede , U.G. ; 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 .
  • 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.
  • 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 , 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 .
  • 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-1H-imidazoles . Chin. Chem. Lett. 2010 , 21 , 429 – 432 .
  • Mukhopadhyay , C. ; Tapaswi , P.K. A Facile and Efficient Synthesis of Tri- and Tetrasubstituted Imidazoles With Potassium Hydrogen Sulfate and DB18C6 in an Aqueous Medium . Green Chem. Lett. Rev. 2012 , 5 , 109 – 120 .
  • 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 .
  • Niralwad , K.S. ; Shingate , B.B. ; Shingare , M.S. Ammonium Metavanadate as an Efficient Catalyst for the Synthesis of 2,4,5-Triaryl-1H-imidazoles . J. Heterocyclic Chem. 2011 , 48 , 742 – 745 .
  • Kurumurthy , C. ; Kumar , G.S. ; Reddy , G.M. ; Nagender , P. ; Rao , P.S. ; Narsaiah , B. A Facile Strategy for the Synthesis of Highly Substituted Imidazole Using Tetrabutyl Ammoniumbromide as Catalyst . Res. Chem. Intermed. 2012 , 38 , 359 – 365 .
  • Tanaka , K. ; Toda , F. Solvent-Free Organic Synthesis . Chem. Rev. 2000 , 100 , 1025 – 1074 .
  • Shi , F. ; Gu , Y. ; Zhang , Q. ; Deng , Y. Development of Ionic Liquids as Green Reaction Media and Catalysts . Catal. Surv. Asia 2004 , 8 , 179 – 186 .
  • Garcia , M.T. ; Gathergood , N. ; Scammells , P.J. Biodegradable Ionic Liquids.Part II. Effect of the Anion and Toxicology . Green Chem. 2005 , 7 , 9 – 14 .
  • Romero , A. ; Santos , A. ; Tojo , J. ; Rodriguez , A. Toxicity and Biodegradability of Imidazolium Ionic Liquids . J. Hazard. Mater. 2008 , 151 , 268 – 273 .
  • Heravi , M.M. ; Zakeri , M. ; Karimi , N. ; Saeedi , M. ; Oskooie , H.A. ; Tavakoli-Hosieni , N. Acidic Ionic Liquid [(CH2)4SO3HMIM][HSO4]: A Green Media for the Simple and Straightforward Synthesis of 2,4,5-Trisubstituted Imidazoles . Synth. Commun. 2010 , 40 , 1998 – 2006 .
  • Shaterian , H.R. ; Ranjbar , M. An Environmental Friendly Approach for the Synthesis of Highly Substituted Imidazoles Using Brønsted Acidic Ionic Liquid, N-Methyl-2-pyrrolidonium Hydrogen Sulfate, as Reusable Catalyst . J. Mol. Liq. 2011 , 160 , 40 – 49 .
  • Zhao , D. ; Wang , Y. ; Duan , E. ; Zhang , J. Oxidation Desulfurization of Fuel Using Pyridinium-Based Ionic Liquids as Phase-Transfer Catalysts . Fuel Process. Technol. 2010 , 91 , 1803 – 1806 .

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.