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Volumn 74, Issue 15, 2009, Pages 5618-5621

Copper-catalyzed cascade addition/cyclization: An efficient and versatile synthesis of N-substituted 2-heterobenzimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

C-N COUPLING; CHEMICAL EQUATIONS; ONE-POT SYNTHESIS;

EID: 68049092041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900743y     Document Type: Article
Times cited : (108)

References (63)
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    • (b) Kodama, T.; Takai, A.; Nakabayashi, M.; Watanabe, L.; Sadaki, H.; Abe, N.; Kurokawa, A. Japanese Patent 50,126,682, 1975; Chem. Abstr. 1976, 84, 44,060.
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    • (a) Takase, Y.; Watanabe, N.; Matsui, M.; Ikuta, H.; Kimura, T.; Saeki, T.; Adachi, H.; Tokumura, T.; Mochida, H.; Akita, Y. Worldwide Patent 93,07,124, 1993; Chem. Abstr. 1993, 119, 203,427.
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    • (b) Takahashi, T.; Kaneko, M.; Kido, Y.; Shibata, T. Japanese Patent 01,063,580, 1989; Chem. Abstr. 1989, 111, 189,568.
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    • Parsons, J. H.; Hunt, R. G.; Leach, S. E.; Percival, A.; Buss, A. D.; Green, D. E.; Mellor, M. European Patent 247,760, 1987; Chem. Abstr. 1987, 108, 131,827.
    • (c) Parsons, J. H.; Hunt, R. G.; Leach, S. E.; Percival, A.; Buss, A. D.; Green, D. E.; Mellor, M. European Patent 247,760, 1987; Chem. Abstr. 1987, 108, 131,827.
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    • Fujishita, T.; Abe, K.; Naito, A.; Makino, I.; Matsumoto, H.; Onodera, N.; Endoh, T.; Iwata, M. Wordwide Patent 2005,121,132, 2005; Chem. Abstr. 2005, 144, 69,828.
    • Fujishita, T.; Abe, K.; Naito, A.; Makino, I.; Matsumoto, H.; Onodera, N.; Endoh, T.; Iwata, M. Wordwide Patent 2005,121,132, 2005; Chem. Abstr. 2005, 144, 69,828.
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    • Axe, F. U.; Bembenek, S. D.; Butler, C. R.; Edwards, J. P.; Fourie, A. M.; Grice, C. A.; Savall, B. M.; Tays, K. L.; Wei, J. M. Worldwide Patent 2005,012,297, 2005; Chem. Abstr. 2005, 142, 219,286.
    • (a) Axe, F. U.; Bembenek, S. D.; Butler, C. R.; Edwards, J. P.; Fourie, A. M.; Grice, C. A.; Savall, B. M.; Tays, K. L.; Wei, J. M. Worldwide Patent 2005,012,297, 2005; Chem. Abstr. 2005, 142, 219,286.
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    • Selected examples for the synthesis of heterocycles via a copper-catalyzed one-pot process: (a) Zhu, J.; Xie, H.; Chen, Z.; Li, S.; Wu, Y. Chem. Commun. 2009, 2338.
    • Selected examples for the synthesis of heterocycles via a copper-catalyzed one-pot process: (a) Zhu, J.; Xie, H.; Chen, Z.; Li, S.; Wu, Y. Chem. Commun. 2009, 2338.
  • 53
    • 68049091408 scopus 로고    scopus 로고
    • Prepared via the aza-Wittig reactions between the corresponding o-haloaryl aza-Wittig reagents and isocyanates. See the Supporting Information.
    • Prepared via the aza-Wittig reactions between the corresponding o-haloaryl aza-Wittig reagents and isocyanates. See the Supporting Information.
  • 54
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    • Several references have described that N,N′-disubstituted carbodiimides could smoothly react with certain N- or O-nucleophiles to give the corresponding adducts under suitable conditions. For the addition with amine see: (a) Park, S. J.; Lee, M. J.; Rhim, H.; Kim, Y.; Lee, J.-H.; Chung, B. Y.; Lee, J. Y. Bioorg. Med. Chem. 2006, 14, 3502.
    • Several references have described that N,N′-disubstituted carbodiimides could smoothly react with certain N- or O-nucleophiles to give the corresponding adducts under suitable conditions. For the addition with amine see: (a) Park, S. J.; Lee, M. J.; Rhim, H.; Kim, Y.; Lee, J.-H.; Chung, B. Y.; Lee, J. Y. Bioorg. Med. Chem. 2006, 14, 3502.
  • 57
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    • For the addition with imidazole see: d
    • For the addition with imidazole see: (d) Ding, M.-W.; Tu, H.-Y.; Liu, Z.-J. Synth. Commun. 1997, 27, 3657.
    • (1997) Synth. Commun , vol.27 , pp. 3657
    • Ding, M.-W.1    Tu, H.-Y.2    Liu, Z.-J.3
  • 59
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    • For the addition with phenol see: f
    • For the addition with phenol see: (f) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 9194.
    • (1999) J. Org. Chem , vol.64 , pp. 9194
    • Larksarp, C.1    Alper, H.2
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    • For details, see the Supporting Information
    • For details, see the Supporting Information.
  • 63
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    • The reactions were carried out in a simple oven-dried round-bottomed flask with a septum and under positive N2 pressure. See the Supporting Information
    • 2 pressure. See the Supporting Information.


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