Water-Accelerated Selective Synthesis of 1,2-Disubstituted Benzimidazoles at Room Temperature Catalyzed by Br⊘nsted Acidic Ionic Liquid

REFERENCES

• Zarrinmayeh , H. ; Nunes , A. M. ; Ornstein , P. L. ; Zimmerman , D. M. ; Arnold , M. B. ; Schober , D. A. ; Bruns , R. F. ; Hipskind , P. A. ; Britton , T. C. ; Cantrell , B. E. ; Gehlert , D. R. Synthesis and evaluation of a series of novel 2-[(4-chlorophenoxy)methyl]benzimidazoles as selective neuropeptide Y Y1 receptor antagonists . J. Med. Chem. 1998 , 41 , 2709 – 2719 .
   PubMed Web of Science ®Google Scholar
• Nakano , H. ; Inoue , T. ; Kawasaki , N. ; Miyataka , H. ; Matsumoto , H. ; Taguchi , T. ; Inagaki , N. ; Nagai , H. ; Satoh , T. Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action . Bioorg. Med. Chem. 2000 , 8 , 373 – 380 .
   PubMed Web of Science ®Google Scholar
• Zhao , Z. S. ; Arnaiz , D. O. ; Griedel , B. ; Sakata , S. ; Dallas , J. L. ; Whitlow , M. ; Trinh , L. ; Post , J. ; Liang , A. ; Morrissey , M. M. ; Shaw , K. J. Design, synthesis, and in vitro biological activity of benzimidazole based factor Xa inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 963–966.
   PubMed Web of Science ®Google Scholar
• White , A. W. ; Almassy , R. ; Calvert , A. H. ; Curtin , N. J. ; Griffin , R. J. ; Hostomsky , Z. ; Maegley , K. ; Newell , D. R. ; Srinivasan , S. ; Golding , B. T. Resistance-modifying agents: 9, Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase . J. Med. Chem. 2000 , 43 , 4084 – 4097 .
   PubMed Web of Science ®Google Scholar
• Zhu , Z. J. ; Lippa , B. ; Drach , J. C. ; Townsend , L. B. Design, synthesis, and biological evaluation of tricyclic nucleosides (dimensional probes) as analogues of certain antiviral polyhalogenated benzimidazole ribonucleosides . J. Med. Chem. 2000 , 43 , 2430 – 2437 .
   PubMed Web of Science ®Google Scholar
• Figge , A. ; Altenbach , H. J. ; Brauer , D. J. ; Tielmann , P. Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-l-isopropyl-1H-benzoimidazole: A new atropisomeric P,N-chelating ligand for asymmetric catalysis . Tetrahedron: Asymmetry 2002 , 13 , 137 – 144 .
   Web of Science ®Google Scholar
• Preston , P. N. Chemistry of Heterocyclic Compounds ; A. Weissberger , E. C. Taylor (Eds.); John Wiley and Sons : New York , 1981 ; vol. 40 .
   Google Scholar
• Chi , Y. C. ; Sun , C. M. Soluble polymer-supported synthesis of a benzimidazole library . Synlett 2000 , 591 – 594 .
   Web of Science ®Google Scholar
• Huang , W. L. ; Scarborough , R. M. A new “traceless” solid-phase synthesis strategy: Synthesis of a benzimidazole library . Tetrahedron Lett. 1999 , 40 , 2665 – 2668 .
   Web of Science ®Google Scholar
• Dudd , L. M. ; Venardou , E. ; Garcia-Verdugo , E. ; Licence , P. ; Blake , A. J. ; Wilson , C. ; Poliakoff , M. Synthesis of benzimidazoles in high-temperature water . Green Chem. 2003 , 5 , 187 – 192 .
   Web of Science ®Google Scholar
• Wu , Z. ; Rea , P. ; Wickam , G. “One-pot” nitro reduction-cyclisation solid phase route to benzimidazoles . Tetrahedron Lett. 2000 , 41 , 9871 – 9874 , and references cited therein .
   Web of Science ®Google Scholar
• Mazurov , A. Traceless synthesis of benzimidazoles on solid support . Bioorg. Med. Chem. Lett. 2000 , 10 , 67 – 70 .
   PubMed Web of Science ®Google Scholar
• Kim , B. H. ; Han , R. B. ; Kim , J. S. ; Jun , Y. M. ; Baik , W. ; Lee , B. M. Indium-mediated reductive intermolecular coupling reaction of 2-nitroaniline with aromatic aldehydes to benzimidazoles . Heterocycles 2004 , 63 , 41 – 54 .
   Web of Science ®Google Scholar
• Perry , R. J. ; Wilson , B. D. A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles . J. Org. Chem. 1993 , 58 , 7016 – 7021 .
   Web of Science ®Google Scholar
• Esser , F. ; Ehrengart , P. ; Ignanatow , H. P. Cyclic guanidines, part 6: Synthesis of benzimidazoles by intramolecular vicarious nucleophilic substitution of hydrogen . J. Chem. Soc., Perkin Trans. 1 1999 , 1153 – 1154 .
   Google Scholar
• Anastasiou , D. ; Campi , E. M. ; Chaouk , H. ; Jackson , W. R. Unusual double hydroformylation of substituted allylanilines leading to the formation of N-arylpyrrolidine aldehydes . Tetrahedron 1992 , 48 , 7467 – 7478 .
   Web of Science ®Google Scholar
• Brain , C. T. ; Brunton , S. A. An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles . Tetrahedron Lett. 2002 , 43 , 1893 – 1895 .
   Web of Science ®Google Scholar
• Perumal , S. ; Mariappan , S. ; Selvaraj , S. A microwave assisted synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in the presence of K-10. Arkivoc 2004, 8, 46–51.
   Web of Science ®Google Scholar
• Chakrabarty , M. ; Mukherjee , R. ; Karmakar , S. ; Harigaya , Y. Tosic acid-on-silica gel: A cheap and eco-friendly catalyst for a convenient one-pot synthesis of substituted benzimidazoles . Monatsh. Chem. 2007 , 138 , 1279 – 1282 .
   Web of Science ®Google Scholar
• Oskooie , H. A. ; Heravi , M. M. ; Sadnia , A. Solventless synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles catalyzed by Fe(ClO4)(3) at room temperature . Chin. Chem. Lett. 2007 , 18 , 1357 – 1360 .
   Web of Science ®Google Scholar
• Varala , R. ; Nasreen , A. ; Enugala , R. ; Adapa , S. R. L-Proline catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles . Tetrahedron Lett. 2007 , 48 , 69 – 72 .
   Web of Science ®Google Scholar
• Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. ; Otokesh , S. ; Baghbanzadeh , M. Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature . Tetrahedron Lett. 2006 , 47 , 2557 – 2560 .
   Web of Science ®Google Scholar
• Wasserscheid , P. ; Welton , T. (Eds.). Ionic Liquids in Synthesis ; Wiley-VCH : Weinheim , 2003 .
   Google Scholar
• Chowdhury , S. ; Mohan , R. S. ; Scott , J. L. Reactivity of ionic liquids . Tetrahedron 2007 , 63 , 2363 – 2389 .
   Web of Science ®Google Scholar
• Wilkes , J. S. Properties of ionic liquid solvents for catalysis . J. Mol. Catal. A: Chem. 2004 , 214 , 11 – 17 .
   Web of Science ®Google Scholar
• Greaves , T. L. ; Drummond , C. J. Protic ionic liquids: Properties and applications . Chem. Rev. 2008 , 108 , 206 – 237 .
   PubMed Web of Science ®Google Scholar
• Dabiri , M. ; Salehi , P. ; Baghbanzadeh , M. ; Zolfigol , M. A. ; Agheb , M. ; Heydari , S. Silica sulfuric acid: An efficient reusable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water and under solvent-free conditions . Catal. Commun. 2008 , 9 , 939 – 942 .
   Web of Science ®Google Scholar
• Dabiri , M. ; Baghbanzadeh , M. ; Nikcheh , M. S. ; Arzroomchilar , E. Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes in water . Bioorg. Med. Chem. Lett. 2008 , 18 , 436 – 438 .
   PubMed Web of Science ®Google Scholar
• Dabiri , M. ; Salehi , P. ; Baghbanzadeh , M. Ionic liquid promoted eco-friendly and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones . Monatsh. Chem. 2007 , 138 , 1191 – 1194 .
   Web of Science ®Google Scholar
• Baghbanzadeh , M. ; Salehi , P. ; Dabiri , M. ; Kozehgary , G. Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives . Synthesis 2006 , 344 – 348 .
   Web of Science ®Google Scholar
• Dabiri , M. ; Salehi , P. ; Baghbanzadeh , M. ; Shakouri , M. ; Otokesh , S. ; Ekrami , T. ; Doosti , R. Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl) methanes, and N-alkyl and N-arylimides in ionic liquids . J. Iran. Chem. Soc. 2007 , 4 , 393 – 401 .
   Web of Science ®Google Scholar
• Dabiri , M. ; Baghbanzadeh , M. ; Arzroomchilar , E. 1-Methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines . Catal. Commun. 2008 , 9 , 939 – 942 .
   Web of Science ®Google Scholar
• Grieco , P. A. Organic Synthesis in Water ; Blackie Academic and Professional : London , 1998 .
   Google Scholar
• Li , C.-J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update. Chem. Rev. 2005, 105, 3095–3166.
   PubMed Web of Science ®Google Scholar
• Narayan , S. ; Muldoon , J. ; Finn , M. G. ; Fokin , V. V. ; Kolb , H. C. ; Sharpless , K. B. “On water”: Unique reactivity of organic compounds in aqueous suspension . Angew. Chem. Int. Ed. 2005 , 44 , 3275 – 3279 .
   PubMed Web of Science ®Google Scholar