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Volumn 68, Issue 17, 2003, Pages 6814-6816

An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLES;

EID: 0043009828     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034824l     Document Type: Article
Times cited : (159)

References (39)
  • 24
    • 0037135994 scopus 로고    scopus 로고
    • Benzimidazoles form the nucleus of many drugs, for example, see: (a) Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A.; Ekker, A.; Yu, X.-H.; Hostomsky, Z.; Webber, S. E.; Eastman, B. W.; Almassy, R.; Li, J.; Curtin, N. J.; Newell, D. R.; Calvert, A. H.; Griffin, R. J.; Golding, B. T. J. Med. Chem. 2003, 46, 210-213. (b) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2002, 12, 2221-2224. (c) Rao, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalà, M. Il Farmaco 2002, 57, 819-823.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2221-2224
    • Valdez, J.1    Cedillo, R.2    Hernández-Campos, A.3    Yépez, L.4    Hernández-Luis, F.5    Navarrete-Vázquez, G.6    Tapia, A.7    Cortés, R.8    Hernández, M.9    Castillo, R.10
  • 25
    • 1842866611 scopus 로고    scopus 로고
    • Benzimidazoles form the nucleus of many drugs, for example, see: (a) Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A.; Ekker, A.; Yu, X.-H.; Hostomsky, Z.; Webber, S. E.; Eastman, B. W.; Almassy, R.; Li, J.; Curtin, N. J.; Newell, D. R.; Calvert, A. H.; Griffin, R. J.; Golding, B. T. J. Med. Chem. 2003, 46, 210-213. (b) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2002, 12, 2221-2224. (c) Rao, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalà, M. Il Farmaco 2002, 57, 819-823.
    • (2002) Il Farmaco , vol.57 , pp. 819-823
    • Rao, A.1    Chimirri, A.2    De Clercq, E.3    Monforte, A.M.4    Monforte, P.5    Pannecouque, C.6    Zappalà, M.7
  • 27
    • 0036738330 scopus 로고    scopus 로고
    • For reviews on the use of microwaves in organic chemistry, see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 717-727
    • Larhed, M.1    Moberg, C.2    Hallberg, A.3
  • 28
    • 0041461964 scopus 로고    scopus 로고
    • For reviews on the use of microwaves in organic chemistry, see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
    • (2002) J. Comb. Chem. , vol.4 , pp. 95-105
    • Lew, A.1    Krutzik, P.O.2    Hart, M.E.3    Chamberlin, A.R.4
  • 29
    • 0037031625 scopus 로고    scopus 로고
    • Hartwig has carried out palladium-catalyzed intermolecular amination reactions using aqueous hydroxide as the base. However, these reactions were carried out in organic solvents with sufficient water only to dissolve the hydroxide, typically 1 equiv. See: Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479-6486.
    • (2002) J. Org. Chem. , vol.67 , pp. 6479-6486
    • Kuwano, R.1    Utsunomiya, M.2    Hartwig, J.F.3
  • 31
    • 0036589259 scopus 로고    scopus 로고
    • For a review of palladium-catalyzed aryl - aryl bond formation, including a summary of aqueous Suzuki reactions, see: Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470.
    • (2002) Chem. Rev. , vol.102 , pp. 1359-1470
    • Hassan, J.1    Sévignon, M.2    Gozzi, C.3    Schulz, E.4    Lemaire, M.5
  • 32
    • 0037134149 scopus 로고    scopus 로고
    • For examples of aqueous Suzuki reactions, see: (a) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722. (b) Badone, D.; Baroni, M.; Cardamone R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
    • (2002) J. Org. Chem. , vol.67 , pp. 2721-2722
    • Sakurai, H.1    Tsukuda, T.2    Hirao, T.3
  • 33
    • 0000586886 scopus 로고    scopus 로고
    • For examples of aqueous Suzuki reactions, see: (a) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722. (b) Badone, D.; Baroni, M.; Cardamone R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
    • (1997) J. Org. Chem. , vol.62 , pp. 7170-7173
    • Badone, D.1    Baroni, M.2    Cardamone, R.3    Ielmini, A.4    Guzzi, U.5
  • 34
    • 12444333847 scopus 로고    scopus 로고
    • note
    • A laboratory microwave instrument with a monomodal cavity and sealed reaction vessels was used: a Smith Creator available from Personal Chemistry AB, Uppsala, Sweden.
  • 35
    • 1842740801 scopus 로고    scopus 로고
    • This is in contrast to observations by Hartwig, see: Hartwig, J. F. Synlett 1997, 329-340.
    • (1997) Synlett , pp. 329-340
    • Hartwig, J.F.1
  • 36
    • 12444281234 scopus 로고    scopus 로고
    • note
    • A control reaction in the absence of any palladium catalyst was carried out. After 167 min at 160 °C a 28% conversion was achieved.
  • 37
    • 12444284014 scopus 로고    scopus 로고
    • note
    • Under these conditions, a thermal comparison was made with use of amidine 1. The reaction was carried out in a sealed microwave vial and was heated in an oil bath, preheated at 160 °C. The reaction mixture was heated for approximately the same time as the reaction carried out in the microwave (approximate due to longer heating and cooling periods). After this time a quantitative conversion to the benzimidazole had been achieved.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.