Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles from θ-Diaminoarene and Aryl Aldehydes

REFERENCES

• (a) Tebbe, M. J.; Spitzer, W. A.; Victor, F.; Miller, S. C.; Lee, C. C.; Sattelberg, T. R.; Mckinney, E.; Tang, C. J. Antirhino/enteroviral vinylacetylene benzimidazoles: A study of their activity and oral plasma levels in mice. J. Med. Chem. 1997, 40, 3937–3946; (b) Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittneben, H.; Entzeroth, M.; van Meel, J. C. A.; Wienen, W.; Hauel, N. H. 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure–activity relationships. J. Med. Chem. 1993, 36, 4040–4051; (c) Fako, V. E.; Wu, X.; Pflug, B.; Liu, J.-Y.; Zhang, J.-T. Repositioning proton pump inhibitors as anticancer drugs by targeting the thioesterase domain of human fatty acid synthase. J. Med. Chem. 2015, 58, 778–784.
   PubMed Web of Science ®Google Scholar
• Denny, W. A.; Rewcastle, G. W.; Bauley, B. C. Potential antitumor agents, 59: Structure–activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II. J. Med. Chem. 1990, 33, 814–819.
   PubMed Web of Science ®Google Scholar
• Gungor, T.; Fouquet, A.; Eulon, J.-M.; Provost, D.; Cazes, M.; Cloarec, A. Cardiotonic agents: Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles. J. Med. Chem. 1992, 35, 4455–4463.
   PubMed Web of Science ®Google Scholar
• Gardiner, J. M.; Loyns, C. R.; Burke, A.; Khan, A.; Mahmood, N. Synthesis and HIV-1 inhibition of novel benzimidazole derivatives. Bioorg. Med. Chem. Lett. 1995, 5, 1251–1254.
   Web of Science ®Google Scholar
• Alonen, A.; Jansson, J.; Kallonen, S.; Kiriazis, A.; Aitio, O.; Finel, M.; Kostiainen, R. Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan. Bioorg. Chem. 2008, 36, 148–155.
   PubMed Web of Science ®Google Scholar
• Elmer, G. I.; Pieper, J. O.; Goldberg, S. R.; George, F. R. Opioid operant self-administration, analgesia, stimulation and respiratory depression in µ-deficient mice. Psychopharmacology (Berlin) 1995, 117, 23–31.
   PubMed Web of Science ®Google Scholar
• Gualtieri, F.; Brody, G.; Fieldsteel, A. H.; Skinner, W. A. Antiviral agents, 2: Analogs of 2-(a-hydroxybenzyl)benzimidazole. J. Med. Chem. 1972, 15, 420–422.
   Web of Science ®Google Scholar
• Mader, M.; De Dios, A.; Shih, C.; Anderson, B. D. Imidazolyl benzimidazoles and imidazo[4,5-b]pyridines as potent p38a MAP kinase inhibitors with excellent in vivo antiinflammatory properties. Bioorg. Med. Chem. Lett. 2008, 18, 179–183.
   PubMed Web of Science ®Google Scholar
• Du, L.-H.; Wang, Y.-G. A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant. Synthesis 2007, 5, 675–678.
   Google Scholar
• Moorthy, J. N.; Neogi, I. IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides. Tetrahedron Lett. 2011, 52, 3868–3871.
   Web of Science ®Google Scholar
• Patil, D. R.; Salunkhe, S. M.; Sambavekar, P. P.; Deshmukh, M. B.; Kolekar, G. B.; Der Anbhule, P. V. Silica sulfuric acid: Recyclable and efficient catalyst for the 2-aryl benzothiazoles. Pharm. Chem. 2011, 3, 189–193.
   Google Scholar
• Chhanda, M.; Pradip Kumar, T. PEG-mediated catalyst-free expeditious synthesis of 2-substituted benzimidazoles and bis-benzimidazoles under solventless conditions. Tetrahedron Lett. 2008, 49, 6237–6240.
   Web of Science ®Google Scholar
• (a) Bommegowda, Y. K.; Lingaraju, G. S.; Thamas, S.; Vinay Kumar, K. S.; Pradeepa Kumara, C. S.; Rangappa, K. S.; Sadashiva, M. P. Weinreb amide as an efficient reagent in the one-pot synthesis of benzimidazoles and benzothiazoles. Tetrahedron Lett. 2013, 54, 2693–2695; (b) Bastug, G.; Eviolitte, C.; Markó, I. E. Functionalized orthoesters as powerful building blocks for the efficient preparation of heteroaromatic bicycles. Org. Lett. 2012, 14, 3502–3505.
   Web of Science ®Google Scholar
• Momeni, A. R.; Samimi, H. A.; Jahanian, R. Urea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation–condensation tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols. Iranian J. Catal. 201 2, 2, 141–145.
   Google Scholar
• Nagasawa, Y.; Matsusaki, Y.; Hotta, T.; Nobuta, T.; Tada, N.; Miura, T.; Itoh, A. Aerobic photooxidative synthesis of benzimidazoles from aromatic aldehydes and diamines using catalytic amounts of magnesium iodide. Tetrahedron Lett. 2014, 55, 6543–6546.
   Web of Science ®Google Scholar
• Pinder, J. L.; Davis, R. E.; Charrier, J.-D. A facile, one-pot procedure for the formation of benzimidazoles from esters using DABAL-Me3, an air stable source of AlMe3. Tetrahedron Lett. 2014, 55, 4853–4855.
   Web of Science ®Google Scholar
• Bahrami, K.; Khodaei, M. M.; Kavianinia, I. A simple and efficient one-pot synthesis of 2-substituted benzimidazoles. Synthesis 2007, 4, 547–550.
   Web of Science ®Google Scholar
• Bahrami, K.; Khodaei, M. M.; Naali, F. Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles. J. Org. Chem. 2008, 73, 6835–6837.
   PubMed Web of Science ®Google Scholar
• Kim, Y.; Kumar, M. R.; Park, N.; Heo, Y.; Lee, S. Copper-catalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C–N bond formation. J. Org. Chem. 2011, 76, 9577–9583.
   PubMed Web of Science ®Google Scholar
• Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. Copper-catalyzed intramolecular C−N bond formation: A straightforward synthesis of benzimidazole derivatives in water. J. Org. Chem. 2011, 76, 716–719.
   PubMed Web of Science ®Google Scholar
• Khan, A. T.; Parvin, T.; Choudhury, L. H. A simple and convenient one-pot synthesis of benzimidazole derivatives using cobalt(II) chloride hexahydrate as catalyst. Synth. Commun. 2009, 39, 2339–2346.
   Web of Science ®Google Scholar
• Curini, M.; Epifano, F.; Montanari, F.; Rosati, O.; Taccone, S. Ytterbium triflate promoted synthesis of benzimidazole derivatives. Synlett, 2004, 10, 1832–1834.
   Web of Science ®Google Scholar
• Trivedi, R.; De, S. K.; Gibbs, R. A. A convenient one-pot synthesis of 2-substituted benzimidazoles. J. Mol. Catal. A: Chem. 2006, 245, 8–11.
   Web of Science ®Google Scholar
• Shingalapur, R. V.; Hosamani, K. M. An efficient and ecofriendly tungstate-promoted zirconia (WOx /ZrO2) solid acid catalyst for the synthesis of 2-aryl benzimidazoles. Catal. Lett. 2010, 137, 63–68.
   Web of Science ®Google Scholar
• Heaney, H.; Newbold, A. J. The oxidation of aromatic aldehydes by magnesium monoperoxyphthalate and urea–hydrogen peroxide. Tetrahedron Lett. 2001, 42, 6607–6609.
   Web of Science ®Google Scholar
• Jeon, B. J.; Kim, K. T.; Kim, S. H. Selective oxidation of sulfides to sulfoxides with cyanuric chloride and urea–hydrogen peroxide adduct. Tetrahedron Lett. 2014, 55, 3905–3908.
   Web of Science ®Google Scholar
• Soldaini, G.; Cardona, F.; Goti, A. Catalytic oxidation of imines based on methyltrioxorhenium/urea hydrogen peroxide: A mild and easy chemo- and regioselective entry to nitrones. Org. Lett. 2007, 9, 473–476.
   PubMed Web of Science ®Google Scholar
• Rong, D.; Phillips, V. A.; Rubio, R. S.; Castro, M. A.; Wheelhouse, R. T. A safe, convenient, and efficient method for the preparation of heterocyclic N-oxides using urea hydrogen peroxide. Tetrahedron Lett. 2008, 49, 6933–6935.
   Web of Science ®Google Scholar
• Varma, R. S.; Naicker, K. P. The urea–hydrogen peroxide complex: Solid-state oxidative protocols for hydroxylated aldehydes and ketones (Dakin reaction), nitriles, sulfides, and nitrogen heterocycles. Org. Lett. 1999, 1, 189–192.
   Web of Science ®Google Scholar
• Caron, S.; Do, N. M.; Sieser, J. E. A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide–urea complex. Tetrahedron Lett. 2000, 41, 2299–2302.
   Web of Science ®Google Scholar