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Volumn 41, Issue 5, 2011, Pages 662-669

Cellulose sulfuric acid: Novel and efficient biodegradable and recyclable acid catalyst for the solid-state synthesis of thiadiazolo benzimidazoles

Author keywords

Benzimidazoles; benzo c 1,2,5 thiadiazole 4,5 diamine; cellulose sulfuric acid; different aldehydes

Indexed keywords

ALDEHYDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZO[C][1,2,5]THIADIAZOLE 4,5 DIAMINE; CELLULOSE DERIVATIVE; DIAMINE DERIVATIVE; SULFURIC ACID; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79551584147     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003632899     Document Type: Article
Times cited : (21)

References (38)
  • 2
    • 5344236080 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists
    • (b) Terzioglu, N.; Rijin, R. M. V.; Bakker, R. A.; Desch, I. J.; Lecurs, R. Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists. Bioorg. Med. Chem. Lett. 2004, 14, 5251.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5251
    • Terzioglu, N.1    Rijin, R.M.V.2    Bakker, R.A.3    Desch, I.J.4    Lecurs, R.5
  • 3
    • 0023152230 scopus 로고
    • In search of the digitalis replacement
    • (a) Erhardt, P. W. In search of the digitalis replacement. J. Med. Chem. 1987, 30, 231;
    • (1987) J. Med. Chem. , vol.30 , pp. 231
    • Erhardt, P.W.1
  • 4
    • 0027744344 scopus 로고
    • 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Syn thesis, biological activity, and structure-activity relationships
    • (b) Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittenben, H.; Entzeroth, M.; Meel, J. C. A. V.; 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;
    • (1993) J. Med. Chem. , vol.36 , pp. 4040
    • Ries, U.J.1    Mihm, G.2    Narr, B.3    Hasselbach, K.M.4    Wittenben, H.5    Entzeroth, M.6    Meel, J.C.A.V.7    Wienen, W.8    Hauel, N.H.9
  • 5
    • 0035905830 scopus 로고    scopus 로고
    • A new class of symmetric bisbenzimidazole-based DNA minor groove binding agents showing antitumor activity
    • (c) Mann, J.; Baron, A.; Opoku-Boahen, Y.; Johansson, E.; Parkinson, G.; Kelland, L. R.; Neidle, S. A new class of symmetric bisbenzimidazole-based DNA minor groove binding agents showing antitumor activity. J. Med. Chem. 2001, 44, 138;
    • (2001) J. Med. Chem. , vol.44 , pp. 138
    • Mann, J.1    Baron, A.2    Opoku-Boahen, Y.3    Johansson, E.4    Parkinson, G.5    Kelland, L.R.6    Neidle, S.7
  • 6
    • 13944252830 scopus 로고    scopus 로고
    • Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1- (b-d-ribofuranosyl) benzimidazole as potential substrates of hPEPT1 transporter
    • (d) Song, X.; Vig, B. S.; Lorenzi, P. L.; Darach, J. C.; Townsend, L. B.; Amiadon, G. L. Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(b-d-ribofuranosyl) benzimidazole as potential substrates of hPEPT1 transporter. J. Med. Chem. 2005, 48, 1274.
    • (2005) J. Med. Chem. , vol.48 , pp. 1274
    • Song, X.1    Vig, B.S.2    Lorenzi, P.L.3    Darach, J.C.4    Townsend, L.B.5    Amiadon, G.L.6
  • 9
    • 0025020286 scopus 로고
    • 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
    • Denny, W. A.; Rewcastle, G. W.; Bagley, 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.
    • (1990) J. Med. Chem. , vol.33 , pp. 814-819
    • Denny, W.A.1    Rewcastle, G.W.2    Bagley, B.C.3
  • 10
    • 0035945983 scopus 로고    scopus 로고
    • A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid: Application of the methodology as a convenient route to benzimidazoles
    • Forseca, T.; Gigante, B.; Gilchrist, T. L. A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid: Application of the methodology as a convenient route to benzimidazoles. Tetrahedron 2001, 57, 1793-1799.
    • (2001) Tetrahedron , vol.57 , pp. 1793-1799
    • Forseca, T.1    Gigante, B.2    Gilchrist, T.L.3
  • 11
    • 0035072011 scopus 로고    scopus 로고
    • Synthesis of 215-hexadecanedione as a precursor of muscone
    • (a) Bai, Y.; Lu, J.; Shi, Z.; Yang, B. Synthesis of 2,15-hexadecanedione as a precursor of muscone. Synlett 2001, 544-546;
    • (2001) Synlett , pp. 544-546
    • Bai, Y.1    Lu, J.2    Shi, Z.3    Yang, B.4
  • 12
    • 0033527812 scopus 로고    scopus 로고
    • Reductive transformation of a,b-epoxy ketones and other compounds promoted through photoinduced electron-transfer processes with 1,3-dimethyl-2- phenylbenzimidazoline (DMPBI)
    • (b) Hasegawa, E.; Yoneoka, A.; Suzuki, K.; Kato, T.; Kitazume, T.; Yangi, K. Reductive transformation of a,b-epoxy ketones and other compounds promoted through photoinduced electron-transfer processes with 1,3-dimethyl-2- phenylbenzimidazoline (DMPBI). Tetrahedron 1999, 55, 12957-12968.
    • (1999) Tetrahedron , vol.55 , pp. 12957-12968
    • Hasegawa, E.1    Yoneoka, A.2    Suzuki, K.3    Kato, T.4    Kitazume, T.5    Yangi, K.6
  • 13
    • 0020384498 scopus 로고
    • Synthesis of benzoxazoles, benzothiazoles, and benzimidazoles and evaluation of their antifungal, insecticidal, and herbicidal activities
    • Hisano, T.; Ichikawa, M.; Tsumoto, K.; Tasaki, M. Synthesis of benzoxazoles, benzothiazoles, and benzimidazoles and evaluation of their antifungal, insecticidal, and herbicidal activities. Chem. Pharm. Bull. 1982, 30, 2996.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 2996
    • Hisano, T.1    Ichikawa, M.2    Tsumoto, K.3    Tasaki, M.4
  • 14
    • 0017872205 scopus 로고
    • Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring: Inhibitors of arginine-specific esteroproteases
    • Tidwell, R. R.; Geratz, J. D.; Dann, O.; Volz, G.; Zeh, D.; Loewe, H. Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring: Inhibitors of arginine-specific esteroproteases. J. Med. Chem. 1978, 21, 613.
    • (1978) J. Med. Chem. , vol.21 , pp. 613
    • Tidwell, R.R.1    Geratz, J.D.2    Dann, O.3    Volz, G.4    Zeh, D.5    Loewe, H.6
  • 15
    • 0032539508 scopus 로고    scopus 로고
    • Single bead IR monitoring of a novel benzimidazole synthesis
    • Sun, Q.; Yan, B. Single bead IR monitoring of a novel benzimidazole synthesis. Bioorg. Med. Chem. Lett. 1998, 8, 361-364.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 361-364
    • Sun, Q.1    Yan, B.2
  • 16
    • 0027769722 scopus 로고
    • A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles
    • (a) Pertry, R. J.; Wilson, B. D. A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles. J. Org. Chem. 1993, 58, 7016-7021;
    • (1993) J. Org. Chem. , vol.58 , pp. 7016-7021
    • Pertry, R.J.1    Wilson, B.D.2
  • 17
    • 0026670474 scopus 로고
    • Synthesis of benzimidazoles containing a fused alicyclic ring by rhodium-catalysed hydroformylation of N-alkenyl-1,2-diaminobenzenes
    • (b) Anastasiou, D.; Campi, E. M.; Chaouk, H.; Jackson, W. R. Synthesis of benzimidazoles containing a fused alicyclic ring by rhodium-catalysed hydroformylation of N-alkenyl-1,2-diaminobenzenes. Tetrahedron 1992, 48, 7467-7478;
    • (1992) Tetrahedron , vol.48 , pp. 7467-7478
    • Anastasiou, D.1    Campi, E.M.2    Chaouk, H.3    Jackson, W.R.4
  • 18
    • 0037017716 scopus 로고    scopus 로고
    • An intramolecular palladiumcatalysed aryl amination reaction to produce benzimidazoles
    • (c) Brain, C. T.; Brunton, S. A. An intramolecular palladiumcatalysed aryl amination reaction to produce benzimidazoles. Tetrahedron Lett. 2002, 43, 1893-1895.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1893-1895
    • Brain, C.T.1    Brunton, S.A.2
  • 19
    • 0034627373 scopus 로고    scopus 로고
    • "One-pot" nitro reduction-cyclisation solid-phase route to benzimidazoles
    • (a) Wu, Z.; Rea, P.; Wickam, G. "One-pot" nitro reduction-cyclisation solid-phase route to benzimidazoles. Tetrahedron Lett. 2000, 41, 9871-9874;
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9871-9874
    • Wu, Z.1    Rea, P.2    Wickam, G.3
  • 20
    • 0034598335 scopus 로고    scopus 로고
    • Traceless synthesis of benzimidazoles on solid support
    • (b) Mazurov, A. Traceless synthesis of benzimidazoles on solid support. Bioorg. Med. Chem. Lett. 2000, 10, 67-70.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 67-70
    • Mazurov, A.1
  • 21
    • 33745685573 scopus 로고    scopus 로고
    • Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles
    • Chakrabarty, M.; Karmakar, S.; Mukherji, A.; Arima, S.; Harigaya, Y. Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles. Heterocycles 2006, 68, 967.
    • (2006) Heterocycles , vol.68 , pp. 967
    • Chakrabarty, M.1    Karmakar, S.2    Mukherji, A.3    Arima, S.4    Harigaya, Y.5
  • 22
    • 28544451672 scopus 로고    scopus 로고
    • An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water
    • Gogoi, P.; Konwar, D. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett. 2006, 47, 79.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 79
    • Gogoi, P.1    Konwar, D.2
  • 23
    • 0035687467 scopus 로고    scopus 로고
    • Traceless solid-phase synthesis of 5-benzoylbenzimidazoles
    • Lee, K. J.; Janda, K. D. Traceless solid-phase synthesis of 5-benzoylbenzimidazoles. Can. J. Chem. 2001, 79, 1556.
    • (2001) Can. J. Chem. , vol.79 , pp. 1556
    • Lee, K.J.1    Janda, K.D.2
  • 24
    • 19544370229 scopus 로고    scopus 로고
    • A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant
    • Lin, S.; Yang, L. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett. 2005, 46, 4315.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4315
    • Lin, S.1    Yang, L.2
  • 25
    • 0043240483 scopus 로고    scopus 로고
    • A practical oxone-mediated, high-throughput, solution-phase synthesis of benzimidazoles from 1,2-phenylenediamines and aldehydes and its application to preparative-scale synthesis
    • Beaulieu, P. L.; Hache, B., Von Moos, E. A practical oxone-mediated, high-throughput, solution-phase synthesis of benzimidazoles from 1,2-phenylenediamines and aldehydes and its application to preparative-scale synthesis. Synthesis 2003, 1683.
    • (2003) Synthesis , pp. 1683
    • Beaulieu, P.L.1    Hache, B.2    Von Moos, E.3
  • 26
    • 0033801916 scopus 로고    scopus 로고
    • Synthetic utility of catalytic Fe(III)=Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bisbenzimidazole, and imidazopyridine derivatives
    • Singh, M. P.; Sasmal, S.; Lu, W.; Chatterjee, M. N. Synthetic utility of catalytic Fe(III)= Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bisbenzimidazole, and imidazopyridine derivatives. Synthesis 2000, 1380.
    • (2000) Synthesis , pp. 1380
    • Singh, M.P.1    Sasmal, S.2    Lu, W.3    Chatterjee, M.N.4
  • 27
    • 31544450237 scopus 로고    scopus 로고
    • A convenient one-pot synthesis of 2-substituted benzimidazoles
    • Trivedi, R.; De, S. K.; Gibbs, R. A. A convenient one-pot synthesis of 2-substituted benzimidazoles. J. Mol. Cat. A: Chem. 2005, 245, 8.
    • (2005) J. Mol. Cat. A: Chem. , vol.245 , pp. 8
    • Trivedi, R.1    De, S.K.2    Gibbs, R.A.3
  • 28
    • 4143104652 scopus 로고    scopus 로고
    • Ytterbium triflate-promoted synthesis of benzimidazole derivatives
    • Massimo, C.; Francesco, E.; Francesca, M. Ytterbium triflate-promoted synthesis of benzimidazole derivatives. Synlett 2004, 1832.
    • (2004) Synlett , pp. 1832
    • Massimo, C.1    Francesco, E.2    Francesca, M.3
  • 29
    • 33644905184 scopus 로고    scopus 로고
    • Synthesis of 2-arylbenzothiazoles and imidazoles using scandium triflate as a catalyst for both a ring closing and an oxidation step
    • Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Synthesis of 2-arylbenzothiazoles and imidazoles using scandium triflate as a catalyst for both a ring closing and an oxidation step. Heterocycles 2004, 63, 2769.
    • (2004) Heterocycles , vol.63 , pp. 2769
    • Itoh, T.1    Nagata, K.2    Ishikawa, H.3    Ohsawa, A.4
  • 30
    • 33749321211 scopus 로고    scopus 로고
    • A simple KHSO4-promoted synthesis of 2-arylsubstituted benzimidazoles by oxidative condensation of aldehydes with o-phenylenediamine
    • Ma, H. Q.; Wang, Y. L.; Wang J. Y. A simple KHSO4-promoted synthesis of 2-arylsubstituted benzimidazoles by oxidative condensation of aldehydes with o-phenylenediamine. Heterocycles 2006, 68, 1669.
    • (2006) Heterocycles , vol.68 , pp. 1669
    • Ma, H.Q.1    Wang, Y.L.2    Wang, J.Y.3
  • 31
    • 33947384926 scopus 로고    scopus 로고
    • Selective synthesis of 2-aryl-1-arylmethyl- 1H-1,3-benzimidazoles promoted by ionic liquid
    • Ma, H. Q.; Wang, Y. L.; Li, J. P.; Wang, J. Y Selective synthesis of 2-aryl-1-arylmethyl- 1H-1,3-benzimidazoles promoted by ionic liquid. Heterocycles 2007, 71, 135.
    • (2007) Heterocycles , vol.71 , pp. 135
    • Ma, H.Q.1    Wang, Y.L.2    Li, J.P.3    Wang, J.Y.4
  • 32
    • 34548650866 scopus 로고    scopus 로고
    • Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot, three-component synthesis of a-amino nitriles
    • Ahmad, S.; Ali, M. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot, three-component synthesis of a-amino nitriles. Appl. Catal. A: Gen. 2007, 331, 149.
    • (2007) Appl. Catal. A: Gen. , vol.331 , pp. 149
    • Ahmad, S.1    Ali, M.2
  • 33
    • 34250009277 scopus 로고    scopus 로고
    • Cellulose sulfuric acid-catalyzed one-pot, three-component synthesis of imidazoazines
    • Ahmad, S.; Ali, M.; Jafar, M. R.; Ebrahim, S. Cellulose sulfuric acid-catalyzed one-pot, three-component synthesis of imidazoazines. Chem. Pharm. Bull. 2007, 55, 957.
    • (2007) Chem. Pharm. Bull. , vol.55 , pp. 957
    • Ahmad, S.1    Ali, M.2    Jafar, M.R.3    Ebrahim, S.4
  • 34
    • 35848937324 scopus 로고    scopus 로고
    • Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines
    • Ahmad, S.; Abbas, R.; Zahra, B. Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines. Catal. Commun. 2008, 9, 13.
    • (2008) Catal. Commun. , vol.9 , pp. 13
    • Ahmad, S.1    Abbas, R.2    Zahra, B.3
  • 35
    • 64849111616 scopus 로고    scopus 로고
    • Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions
    • Venu Madhav, J.; Thirupathi Reddy, Y.; Narsimha Reddy, P.; Nikhil Reddy, M.; Suresh, K.; Crooks, P. A.; Rajitha, B. Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions. J. Mol. Catal. A 2009, 304, 85-87.
    • (2009) J. Mol. Catal. A , vol.304 , pp. 85-87
    • Venu Madhav, J.1    Thirupathi Reddy, Y.2    Narsimha Reddy, P.3    Nikhil Reddy, M.4    Suresh, K.5    Crooks, P.A.6    Rajitha, B.7
  • 36
    • 61949366035 scopus 로고    scopus 로고
    • Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones
    • Narsimha Reddy, P.; Thirupathi Reddy, Y.; Nikhil Reddy, M.; Rajitha, B.; Crooks, P. A. cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)- ones. Synth. Commun. 2009, 39, 1257.
    • (2009) Synth. Commun. , vol.39 , pp. 1257
    • Narsimha Reddy, P.1    Thirupathi Reddy, Y.2    Nikhil Reddy, M.3    Rajitha, B.4    Crooks, P.A.5
  • 38
    • 47349105235 scopus 로고    scopus 로고
    • Dipyridine copper chloride as a mild and efficient catalyst for the solid state-synthesis of 2-substituted benzimidazoles
    • Venu Madhav, J.; Suresh Kuarm, B.; Rajitha, B. Dipyridine copper chloride as a mild and efficient catalyst for the solid state-synthesis of 2-substituted benzimidazoles. Arkivoc 2008, 13, 145-150.
    • (2008) Arkivoc , vol.13 , pp. 145-150
    • Venu Madhav, J.1    Suresh Kuarm, B.2    Rajitha, B.3


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