Synthesis of Some Novel 1,2-Disubstituted Benzimidazole-5-carboxylates via One-Pot Method Using Sodium Dithionite and Its Effect on N-Debenzylation

REFERENCES

• Goker , H. ; Kus , C. ; Boykin , D. W. ; Yildiz , S. ; Altanlar , N. Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species . Bioorg. Med. Chem. 2002 , 10 , 2589 – 2596 .
   PubMed Web of Science ®Google Scholar
• Evans , D. ; Hicks , T. A. ; Williamson , W. R. N. ; Dawson , W. ; Meacock , S. C. R. ; Kitchen , E. A. Synthesis of a group of 1H–benzimidazoles and their screening for anti-inflammatory activity . Eur. J. Med. Chem. 1996 , 31 , 635 – 642 .
   Web of Science ®Google Scholar
• Nakano , H. ; Inoue , T. ; Kawasaki , N. ; Miyataka , H. ; Matsumoto , H. ; Taguchi , T. ; Inagaki , N. ; Nagai , H. ; Satoh , T. Synthesis of benzimidazole derivatives as antiallergic agents with 5-lipoxygenase inhibiting action . Chem. Pharm. Bull. 1999 , 47 , 1573 – 1578 .
   PubMedGoogle Scholar
• Kus , C. ; Ayhan-Kilcigil , G. ; Can-Eke , B. ; Iscan , M. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver . Arch. Pharm. Res. 2004 , 27 , 156 – 163 .
   PubMed Web of Science ®Google Scholar
• Mohamed , B. G. ; Hussein , M. A. ; Abdel-Alim , A. M. ; Hashem , M. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1,2,4-triazolobenzimidazole derivatives . Arch. Pharm. Res. 2006 , 29 , 26 – 33 .
   PubMedGoogle Scholar
• Denny , W. A. ; Rewcastle , G. W. ; Baguley , 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
• Mavrova , A. T. ; Anichina , K. K. ; Vuchev , D. I. ; Tsenov , J. A. ; Denkova , P. S. ; Kondeva , M. S. ; Micheva , M. K. Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives . Eur. J. Med. Chem. 2006 , 41 , 1412 – 1420 .
   PubMed Web of Science ®Google Scholar
• Victor , F. ; Brown , T. J. ; Campanale , K. ; Heinz , B. A. ; Shipley , L. A. ; Su , K. S. ; Tang , J. ; Vance , L. M. ; Spitzer , W. A. Synthesis, antiviral activity, and biological properties of vinylacetylene analogs of enviroxime . J. Med. Chem. 1997 , 40 , 151 – 1518 .
   Google Scholar
• Camacho , J. ; Barazarte , A. ; Gamboa , N. ; Rodrigues , J. ; Rojas , R. ; Vaisberg , A. ; Gilman , R. ; Charris , J. Synthesis and biological evaluation of benzimidazole-5- carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents . Bioorg. Med. Chem. 2011 , 19 , 2023 – 2029 .
   PubMed Web of Science ®Google Scholar
• Beaulieu , P. L. ; Gillard , J. ; Bykowski , D. ; Brochu , C. ; Dansereau , N. ; Duceppe , J. S. ; Hache , B. ; Jakalian , A. ; Lagace , L. ; LaPlante , S. ; McKercher , G. ; Moreau , E. ; Perreault , S. ; Stammers , T. ; Thauvette , L. ; Warrington , J. ; Kukolj , G. Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCV NS5B polymerase: From benzimidazole to indole scaffolds . Bioorg. Med. Chem. Lett. 2006 , 14 , 4987 – 5002 .
   Web of Science ®Google Scholar
• Hirashima , S. ; Suzuki , T. ; Ishida , T. ; Noji , S. ; Yata , S. ; Ando , I. ; Komatsu , M. ; Ikeda , S. ; Hashimoto , H. Benzimidazole derivatives bearing substituted biphenyls as hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitors: Structure–activity relationship studies and identification of a potent and highly selective inhibitor JTK-109 . J. Med. Chem. 2006 , 49 , 4721 – 4736 .
   PubMed Web of Science ®Google Scholar
• Vanden , E. J. J. , Delfosse , Lor , F.P. ; Haverbeke , Y. V. 2,3-Dichloro.5,6-dicyano- l,4-benzoquinone, a mild catalyst for the formation of carbon–nitrogen bonds. Tetrahedron 1995, 51, 5813.
   Web of Science ®Google Scholar
• Gill , C. ; Jadhav , G. ; Shaikh , M. ; Kale , R. ; Ghawalkar , A. ; Nagargoje , D. ; Shiradkar , M. Clubbed [1,2,3]-triazoles by fluorine benzimidazole: A novel approach to H37Rv inhibitors as a potential treatment for tuberculosis . Bioorg. Med. Chem. Lett. 2008 , 18 , 6244 – 6247 .
   PubMed Web of Science ®Google Scholar
• Preston , P. N. ; Weissberger , A. ; Taylor , E. C. In Chemistry of Heterocyclic Compounds, Part 1 ; John Wiley and Sons : New York , 1981 ; vol. 40 , p. 6 – 60 .
   Google Scholar
• Grimmet , M. R. In Comprehensive Heterocyclic Chemistry ; A. R. Katritzky , C. W. Rees (Eds.); Pergamon Press : Oxford , 1984 ; vol. 5 , p. 457 .
   Google Scholar
• Tandon , V. K. ; Kumar , M. BF3 · Et2O-promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines . Tetrahedron Lett. 2004 , 45 , 4185 – 4187 .
   Web of Science ®Google Scholar
• Tempest , P. ; Ma , V. ; Thomas , S. ; Hua , Z. ; Kelly , M. G. ; Hulme , C. Two-step solution-phase synthesis of novel benzimidazoles utilizing a UDC (Ugi/de-Boc/cyclize) strategy . Tetrahedron Lett. 2001 , 42 , 4959 – 4962 .
   Web of Science ®Google Scholar
• Inamdar , S. M. ; More , V. K. ; Mandal , S. K. CuO nano-particles supported on silica, a new catalyst for facile synthesis of benzimidazoles, benzothiazoles, and benzoxazoles . Tetrahedron Lett. 2013 , 54 , 579 – 583 .
   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 .
   Web of Science ®Google Scholar
• Hornberger , K. R. ; Adjabeng , G. M. ; Dickson , H. D. ; Davis-Ward , R. G. A mild, one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines . Tetrahedron Lett. 2006 , 47 , 5359 – 5361 .
   Web of Science ®Google Scholar
• Van Vliet , D. S. ; Gillespie , P. ; Scicinski , J. J. Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions . Tetrahedron Lett. 2005 , 46 , 6741 – 6743 .
   Web of Science ®Google Scholar
• Kim , B. H. ; Han , R. ; 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
• Surpur , M. P. ; Singh , P. R. ; Patil , S. B. ; Samant , S. D. One‐pot synthesis of benzimidazoles from o‐nitroanilines under microwaves via a reductive cyclization . Synth. Commun. 2007 , 37 , 1375 – 1379 .
   Web of Science ®Google Scholar
• Yang , D. ; Fokas , D. ; Li , J. ; Yu , L. ; Baldino , C. M. A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization . Synthesis 2005 , 47 – 56 .
   Web of Science ®Google Scholar
• Zhou , B. ; Li , B. ; Yi , W. ; Bu , X ; Ma , L. Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives . Bioorg. Med. Chem. Lett. 2013 , 23 , 3759 – 3763 .
   PubMed Web of Science ®Google Scholar
• Oda , S. ; Shimizu , H. ; Aoyama , Y. ; Ueki , T. ; Shimizu , S. ; Osato , H. ; Takeuchi , Y. Development of safe one-pot synthesis of N-1- and C-2-substituted benzimidazole via reductive cyclization of o-nitroarylamine using Na2S2O4 . Org. Process Res. Dev. 2012 , 16 , 96 – 101 .
   Web of Science ®Google Scholar
• Adinolfi , M. ; Barone , G. ; Guariniello , L. ; Iadonisi , A. Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two- phase conditions . Tetrahedron Lett. 1999 , 40 , 8439 – 8441 .
   Web of Science ®Google Scholar
• Senthilkumar , P. M. ; Aravind , A. ; Baskaran , S. Regioselective oxidative cleavage of benzylidene acetal: New synthesis of α- and β-benzoyloxy carboxylic acids . Tetrahedron Lett. 2007 , 48 , 1175 – 1178 .
   Web of Science ®Google Scholar