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Volumn 42, Issue 20, 2012, Pages 2981-2993

One-pot synthesis of 1 H-benzimidazole derivatives using thiamine hydrochloride as a reusable organocatalyst

Author keywords

1 H benzimidazole; Aldehyde; green chemistry; o phenylenediamine; thiamine hydrochloride (VB 1

Indexed keywords

ALDEHYDE; BENZIMIDAZOLE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PHENYLENEDIAMINE; THIAMINE;

EID: 84862872784     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.573610     Document Type: Article
Times cited : (36)

References (39)
  • 1
    • 0017915202 scopus 로고
    • Halobenzimidazole ribosides and RNA synthesis of cells and viruses
    • (a) Tamm, I.; Sehgal, P. B. Halobenzimidazole ribosides and RNA synthesis of cells and viruses. Adv. Virus Res. 1978, 22, 187-258;
    • (1978) Adv. Virus Res. , vol.22 , pp. 187-258
    • Tamm, I.1    Sehgal, P.B.2
  • 2
    • 0040482632 scopus 로고
    • Inhibition of influenza and mumps virus multiplication by 4,5,6-(or 56,7-) trichloro-1-b-D-ribofuranosylbenzimidazole
    • (b) Tamm, I. Inhibition of influenza and mumps virus multiplication by 4,5,6-(or 5,6,7-) trichloro-1-b-D-ribofuranosylbenzimidazole. Science 1957, 126, 1235-1236;
    • (1957) Science , vol.126 , pp. 1235-1236
    • Tamm, I.1
  • 4
    • 0032499278 scopus 로고    scopus 로고
    • Design synthesis, and antiviral activity of r-nucleosides: D-and L-isomers of lyxofuranosyl-and (5-deoxylyxofuranosyl) benzimidazoles
    • (d) Migawa, M. T.; Giradet, J. L.; Walker, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B. Design, synthesis, and antiviral activity of r-nucleosides: D-and L-isomers of lyxofuranosyl-and (5-deoxylyxofuranosyl) benzimidazoles. J. Med. Chem. 1998, 41, 1242-1251;
    • (1998) J. Med. Chem. , vol.41 , pp. 1242-1251
    • Migawa, M.T.1    Giradet, J.L.2    Walker, J.A.3    Koszalka, G.W.4    Chamberlain, S.D.5    Drach, J.C.6    Townsend, L.B.7
  • 5
    • 0032499283 scopus 로고    scopus 로고
    • Design synthesis and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5 6-dichlorobenzimidazoles as nonnucleoside analogues of 2 5,6-trichloro-1-(a-D-ribofuranosyl) benzimidazole
    • (e) Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-trichloro-1-(a-D-ribofuranosyl) benzimidazole. J. Med. Chem. 1998, 41, 1252-1261.
    • (1998) J. Med. Chem. , vol.41 , pp. 1252-1261
    • Porcari, A.R.1    Devivar, R.V.2    Kucera, L.S.3    Drach, J.C.4    Townsend, L.B.5
  • 7
    • 0031463691 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel nonnucleoside inhibitors of HIV1 reverse transcriptase: 2-Aryl-substituted benzimidazoles
    • Roth, M.; Morningstar M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W. Jr.; Michejda, C. J. Synthesis and biological activity of novel nonnucleoside inhibitors of HIV1 reverse transcriptase: 2-Aryl-substituted benzimidazoles. J. Med. Chem. 1997, 40 4199-4207.
    • (1997) J. Med. Chem. , vol.40 , pp. 4199-4207
    • Roth, M.1    Morningstar, M.L.2    Boyer, P.L.3    Hughes, S.H.4    Buckheit Jr., R.W.5    Michejda, C.J.6
  • 8
    • 4143112939 scopus 로고
    • Benzimidazoles and congeneric tricyclic compounds
    • A. Weissberger, and E. C. Taylor (Eds.); Wiley: New York
    • (b) Preston, P. N. Benzimidazoles and congeneric tricyclic compounds; In The Chemistry of Heterocyclic Compounds, Part 1; A. Weissberger, and E. C. Taylor (Eds.); Wiley: New York, 1981; vol. 40, pp. 6-60.
    • (1981) The Chemistry of Heterocyclic Compounds, Part 1 , vol.40 , pp. 6-60
    • Preston, P.N.1
  • 9
    • 84943408843 scopus 로고
    • Imidazoles and their benzo derivatives
    • A. R. Katritzky; and C. W. Rees (Eds.); Pergamon: Oxford
    • Grimmett, M. R. Imidazoles and their benzo derivatives; In Comprehensive Heterocyclic Chemistry; A. R. Katritzky; and C. W. Rees (Eds.); Pergamon: Oxford, 1984; vol. 5, pp. 457-487.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 457-487
    • Grimmett, M.R.1
  • 11
    • 4143063050 scopus 로고
    • Convenient routes to substituted benzimidazoles and imidazolo[ 4,5-b]pyridines using nitrobenzene as oxidant
    • (a) Yadagiri, B.; Lown, J. W. Convenient routes to substituted benzimidazoles and imidazolo[4,5-b]pyridines using nitrobenzene as oxidant. Synth. Commun. 1990, 20, 955-963;
    • (1990) Synth. Commun. , vol.20 , pp. 955-963
    • Yadagiri, B.1    Lown, J.W.2
  • 12
    • 0032539508 scopus 로고    scopus 로고
    • Single bead IR monitoring of a novel benzimidazole synthesis
    • DOI 10.1016/S0960-894X(98)00024-9, PII S0960894X98000249
    • (b) Sun, Q.; Yan, B. Single-bead IR monitoring of a novel benzimidazole synthesis. Bioorg. Med. Chem. Lett. 1998, 8, 361-364. (Pubitemid 28072707)
    • (1998) Bioorganic and Medicinal Chemistry Letters , vol.8 , Issue.4 , pp. 361-364
    • Sun, Q.1    Yan, B.2
  • 13
    • 0345761268 scopus 로고    scopus 로고
    • Synthesis of 2-subsituted benzimidazoles by reaction of o-phenylenediamine with aldehydes in the presence of Sc(OTf) 3
    • Nagata, K.; Itoh, T.; Ishikawa, H.; Ohsawa, A. Synthesis of 2-subsituted benzimidazoles by reaction of o-phenylenediamine with aldehydes in the presence of Sc(OTf)3. Heterocycles 2003, 61, 93-96.
    • (2003) Heterocycles , Issue.61 , pp. 93-96
    • Nagata, K.1    Itoh, T.2    Ishikawa, H.3    Ohsawa, A.4
  • 14
    • 4143104652 scopus 로고    scopus 로고
    • Ytterbium triflate promoted synthesis of benzimidazole derivatives
    • Currini, M.; Epifana, F.; Montanari, F.; Rosati, O.; Taccone, S. Ytterbium triflate-promoted synthesis of benzimidazole derivatives. Synlett 2004, 1832-1834. (Pubitemid 39099700)
    • (2004) Synlett , Issue.10 , pp. 1832-1834
    • Curini, M.1    Epifano, F.2    Montanari, F.3    Rosati, O.4    Taccone, S.5
  • 15
    • 85162691835 scopus 로고
    • Eine neue synthese von benzimidazol derivaten
    • Weidenhagen, R. Eine neue synthese von benzimidazol derivaten. Ber. 1936, 69, 2263-2266.
    • (1936) Ber. , vol.69 , pp. 2263-2266
    • Weidenhagen, R.1
  • 16
    • 0029061671 scopus 로고
    • 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds
    • Eynde, J. J. V.; Delfosse, F.; Lor, P.; Haverbeke, Y. V. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron 1995, 51, 5813-5818.
    • (1995) Tetrahedron , vol.51 , pp. 5813-5818
    • Eynde, J.J.V.1    Delfosse, F.2    Lor, P.3    Haverbeke, Y.V.4
  • 17
    • 28544451672 scopus 로고    scopus 로고
    • An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water
    • DOI 10.1016/j.tetlet.2005.10.134, PII S0040403905023907
    • Gogio, P.; Konwar, D. An efficient and one-pot synthesis of imidazoles and benzimidazoles via anaerobic oxidation of carbonnitrogen bonds in water. Tetrahedron Lett. 2006, 47, 79-82. (Pubitemid 41743780)
    • (2006) Tetrahedron Letters , vol.47 , Issue.1 , pp. 79-82
    • Gogoi, P.1    Konwar, D.2
  • 18
    • 34948893906 scopus 로고    scopus 로고
    • One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-triaryl-1H-imidazoles using oxalic acid catalyst
    • DOI 10.1055/s-2007-983872
    • 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. (Pubitemid 47528863)
    • (2007) Synthesis , Issue.18 , pp. 2829-2834
    • Kokare, N.D.1    Sangshetti, J.N.2    Shinde, D.B.3
  • 19
    • 33751419514 scopus 로고    scopus 로고
    • L-Proline-catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H- benzimidazoles
    • 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.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 69-72
    • Varala, R.1    Nasreen, A.2    Enugala, R.3    Adapa, S.R.4
  • 20
    • 43049181336 scopus 로고    scopus 로고
    • Synthesis of condensed benzo[NN]-heterocycles by microwave-assisted solid acid catalysis
    • Landge, S. M.; Törö k, B. Synthesis of condensed benzo[N,N]-heterocycles by microwave-assisted solid acid catalysis. Catal. Lett. 2008, 122, 338-343.
    • (2008) Catal. Lett. , vol.122 , pp. 338-343
    • Landge, S.M.1    Török, B.2
  • 21
    • 50649083250 scopus 로고    scopus 로고
    • M(HSO4) n-promoted synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazole derivatives
    • Niknam, K.; Zolfigol, M. A.; Safikhani, N. M(HSO4)n-promoted synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazole derivatives. Synth. Commun. 2008, 38, 2919-2928.
    • (2008) Synth. Commun. , vol.38 , pp. 2919-2928
    • Niknam, K.1    Zolfigol, M.A.2    Safikhani, N.3
  • 23
    • 0347024188 scopus 로고    scopus 로고
    • Indium-mediated reductive intermolecular coupling reaction of 2-nitroaniline with aromatic aldehydes to benzimidazoles
    • (a) 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;
    • (2004) Heterocycles , vol.63 , pp. 41-54
    • Kim, B.H.1    Han, R.2    Kim, J.S.3    Jun, Y.M.4    Baik, W.5    Lee, B.M.6
  • 24
    • 12344311063 scopus 로고    scopus 로고
    • A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization
    • DOI 10.1055/s-2004-834926, M02904SS
    • (b) Yang, D. L.; Fokas, D.; Li, J. Z.; Yu, L. B.; 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; (Pubitemid 40128421)
    • (2005) Synthesis , Issue.1 , pp. 47-56
    • Yang, D.1    Fokas, D.2    Li, J.3    Yu, L.4    Baldino, C.M.5
  • 25
    • 0037017716 scopus 로고    scopus 로고
    • An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles
    • DOI 10.1016/S0040-4039(02)00132-6, PII S0040403902001326
    • (c) Brain, C. T.; Brunton, S. A. An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles. Tetrahedron Lett. 2002, 43, 1893-1895; (Pubitemid 34175195)
    • (2002) Tetrahedron Letters , vol.43 , Issue.10 , pp. 1893-1895
    • Brain, C.T.1    Brunton, S.A.2
  • 26
    • 0037631073 scopus 로고    scopus 로고
    • Synthèse chimiosélective des benzimidazoles sur silice traitée par le chlorure du thionyle
    • DOI 10.1016/S0040-4039(03)01387-X
    • (d) Alloum, A. B.; Bougrin, K.; Soufiaoui, M. Synthèse chimiosé lective des benzimidazoles sur silice traitée par le chlorure du thionyle. Tetrahedron Lett. 2002, 44, 5935-5937; (Pubitemid 36829242)
    • (2003) Tetrahedron Letters , vol.44 , Issue.31 , pp. 5935-5937
    • Alloum, A.B.1    Bougrin, K.2    Soufiaoui, M.3
  • 27
    • 77956226354 scopus 로고    scopus 로고
    • Nanoporous aluminosilicate catalyst with 3D cage-type porous structure as an efficient catalyst for the synthesis of benzimidazole derivatives
    • (e) Chari, M. A.; Shobha, D.; Kenawy, E. R.; Al-Deyab, S. S.; Reddy, B. V. S.; Vinu, A. Nanoporous aluminosilicate catalyst with 3D cage-type porous structure as an efficient catalyst for the synthesis of benzimidazole derivatives. Tetrahedron Lett. 2010, 51, 5195-5199.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 5195-5199
    • Chari, M.A.1    Shobha, D.2    Kenawy, E.R.3    Al-Deyab, S.S.4    Reddy, B.V.S.5    Vinu, A.6
  • 28
    • 77955494715 scopus 로고    scopus 로고
    • Polyethylene glycol: A recyclable solvent system for the synthesis of benzimidazole derivatives using CAN as catalyst
    • (f) Kidwai, M.; Jahan, A.; Bhatnagar, D. Polyethylene glycol: A recyclable solvent system for the synthesis of benzimidazole derivatives using CAN as catalyst. J. Chem. Sci. 2010, 122, 607-612;
    • (2010) J. Chem. Sci. , vol.122 , pp. 607-612
    • Kidwai, M.1    Jahan, A.2    Bhatnagar, D.3
  • 29
    • 38949118738 scopus 로고    scopus 로고
    • Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines
    • (f) Zhang, Z.-H.; Li, J.-J.; Gao, Y.-Z.; Liu, Y.-H. Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines. J. Heterocycl. Chem. 2007, 44, 1509-1512; (Pubitemid 351225793)
    • (2007) Journal of Heterocyclic Chemistry , vol.44 , Issue.6 , pp. 1509-1512
    • Zhang, Z.-H.1    Li, J.-J.2    Gao, Y.-Z.3    Liu, Y.-H.4
  • 30
    • 33846026688 scopus 로고    scopus 로고
    • A highly effective sulfamic acid = methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature
    • (h) Zhang, Z.-H.; Li, T.-S.; Li, J.-J. A highly effective sulfamic acid = methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature. Monatsh. Chem. 2007, 138, 89-94.
    • (2007) Monatsh. Chem. , vol.138 , pp. 89-94
    • Zhang, Z.-H.1    Li, T.-S.2    Li, J.-J.3
  • 31
    • 23044493101 scopus 로고    scopus 로고
    • Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4- dihydropyrimidin-2-(1H)-ones under solvent-free conditions
    • DOI 10.1055/s-2005-869899, M00305SS
    • De, S. K.; Gibbs, R. A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones under solvent-free conditions. Synthesis 2005, 1748-1750. (Pubitemid 41058553)
    • (2005) Synthesis , Issue.11 , pp. 1748-1750
    • De, S.K.1    Gibbs, R.A.2
  • 32
    • 43449087317 scopus 로고    scopus 로고
    • Nucleophilic carbene-catalysed oxidative esterification reactions
    • (a) Noonan, C.; Baragwanath, L.; Connon, S. J. Nucleophilic carbene-catalysed oxidative esterification reactions. Tetrahedron Lett. 2008, 49, 4003-4006;
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4003-4006
    • Noonan, C.1    Baragwanath, L.2    Connon, S.J.3
  • 34
    • 0345490784 scopus 로고    scopus 로고
    • 2-symmetric N-alkyl-benzimidazolium and thiazolium salts
    • DOI 10.1016/j.tetasy.2003.09.050
    • (c) Orlandi, S.; Caporale, M.; Benaglia, M.; Annunziata, R. Synthesis of new enantiomerically pure C1-and C2-symmetric N-alkyl-benzimidazolium and thiazolium salts. Tetrahedron: Asymmetry 2003, 14, 3827-3830; (Pubitemid 37500880)
    • (2003) Tetrahedron Asymmetry , vol.14 , Issue.24 , pp. 3827-3830
    • Orlandi, S.1    Caporale, M.2    Benaglia, M.3    Annunziata, R.4
  • 35
    • 70349478611 scopus 로고    scopus 로고
    • Thiamine hydrochloride as a efficient catalyst for the synthesis of amidoalkyl naphthols
    • (d) Lei, M.; Ma, L.; Hu, L. Thiamine hydrochloride as a efficient catalyst for the synthesis of amidoalkyl naphthols. Tetrahedron Lett. 2009, 50, 6393-6397;
    • (2009) Tetrahedron Lett. , vol.50 , pp. 6393-6397
    • Lei, M.1    Ma, L.2    Hu, L.3
  • 36
    • 77955306565 scopus 로고    scopus 로고
    • A convenient one-pot synthesis of formamide derivatives using thiamine hydrochloride as a novel catalyst
    • (e) Lei, M.; Ma, L.; Hu, L. A convenient one-pot synthesis of formamide derivatives using thiamine hydrochloride as a novel catalyst. Tetrahedron Lett. 2010, 51, 4186-4188;
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4186-4188
    • Lei, M.1    Ma, L.2    Hu, L.3
  • 37
    • 77953121810 scopus 로고    scopus 로고
    • An efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by thiamine hydrochloride in water under ultrasound irradiation
    • (f) Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H. An efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by thiamine hydrochloride in water under ultrasound irradiation. Tetrahedron Lett. 2010, 51, 3138-3140.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 3138-3140
    • Mandhane, P.G.1    Joshi, R.S.2    Nagargoje, D.R.3    Gill, C.H.4
  • 38
    • 60849100224 scopus 로고    scopus 로고
    • Practical ecofriendly, and chemoselective method for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using amberlite IR-120 as a reusable heterogeneous catalyst in aqueous media
    • Sharma, S. D.; Komwar, D. Practical, ecofriendly, and chemoselective method for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using amberlite IR-120 as a reusable heterogeneous catalyst in aqueous media. Synth. Commun. 2009, 39, 980-991.
    • (2009) Synth. Commun. , vol.39 , pp. 980-991
    • Sharma, S.D.1    Komwar, D.2
  • 39
    • 39449106574 scopus 로고    scopus 로고
    • Bismuth(III)-catalyzed rapid and highly efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles in water
    • Yadav, J. S.; Reddy, B. V. S.; Premalatha, K.; Shankar, K. S. Bismuth(III)-catalyzed rapid and highly efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles in water. Can. J. Chem. 2008, 86, 124.
    • (2008) Can. J. Chem. , vol.86 , pp. 124
    • Yadav, J.S.1    Reddy, B.V.S.2    Premalatha, K.3    Shankar, K.S.4


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