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Ruthenium-Catalyzed Synthesis of Benzimidazoles from N-Alkyl-1,2-diaminobenzenes via Alkyl Group Transfer

  • Cho, Chan-Sik (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Jun-Uk (Department of Applied Chemistry, Kyungpook National University)
  • Published : 2008.06.20

Abstract

Keywords

References

  1. Grimmett, M. R. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon: Oxford, New York, 1979; Vol. 4, p 357
  2. Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 3, p 77
  3. Grimmett, M. R. In Imidazole and Benzimidazole Synthesis; Academic Press: London, 1997
  4. Kondo, T.; Yang, S.; Huh, K.-T.; Kobayashi, M.; Kotachi, S.; Watanabe, Y. Chem. Lett. 1991, 1275
  5. Wilfred, C. D.; Taylor, R. J. K. Synlett 2004, 1628
  6. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576
  7. Cho, C. S.; Kim, B. T.; Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997 https://doi.org/10.1016/j.tet.2003.08.027
  8. Cho, C. S.; Oh, S. G. Tetrahedron Lett. 2006, 47, 5633 https://doi.org/10.1016/j.tetlet.2006.06.038
  9. Cho, C. S.; Ren, W. X.; Shim, S. C. Tetrahedron Lett. 2006, 47, 6781 https://doi.org/10.1016/j.tetlet.2006.07.067
  10. Perry, R. J.; Wilson, B. D. J. Org. Chem. 1993, 58, 7016 https://doi.org/10.1021/jo00077a019
  11. Brain, C. T.; Brunton, S. A. Tetrahedron Lett. 2002, 43, 1893 https://doi.org/10.1016/S0040-4039(02)00132-6
  12. Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499 https://doi.org/10.1016/S0040-4039(98)02661-6
  13. Cho, C. S.; Oh, B. H.; Shim, S. C. J. Heterocycl. Chem. 1999, 36, 1175 https://doi.org/10.1002/jhet.5570360510
  14. Cho, C. S.; Kim, J. S.; Oh, B. H.; Kim, T.-J.; Shim, S. C. Tetrahedron 2000, 56, 7747 https://doi.org/10.1016/S0040-4020(00)00694-3
  15. Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885
  16. Cho, C. S.; Kim, T. K.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Organomet. Chem. 2002, 650, 65 https://doi.org/10.1016/S0022-328X(02)01170-1
  17. Cho, C. S.; Lim, H. K.; Shim, S. C.; Kim, T. J.; Choi, H.-J. Chem. Commun. 1998, 995
  18. Cho, C. S.; Kim, J. H.; Shim, S. C. Tetrahedron Lett. 2000, 41, 1811 https://doi.org/10.1016/S0040-4039(00)00035-6
  19. Cho, C. S.; Kim, J. H.; Kim, T.-J.; Shim, S. C. Tetrahedron 2001, 57, 3321 https://doi.org/10.1016/S0040-4020(01)00202-2
  20. Cho, C. S.; Kim, B. T.; Lee, M. J.; Kim, T.-J.; Shim, S. C. Angew. Chem. Int. Ed. 2001, 40, 958 https://doi.org/10.1002/1521-3773(20010302)40:5<958::AID-ANIE958>3.0.CO;2-4
  21. Cho, C. S. Catal. Commun. 2006, 7, 1012 https://doi.org/10.1016/j.catcom.2006.05.005
  22. Murahashi, S.-I. Angew. Chem. Int. Ed. 1995, 34, 2443 https://doi.org/10.1002/anie.199524431
  23. Murahashi, S.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002 https://doi.org/10.1021/ja00353a025
  24. Rai, R.; Pandey, P. S. Bioorg. & Med. Chem. Lett. 2005, 15, 2923 https://doi.org/10.1016/j.bmcl.2005.03.097
  25. Cho, C. S.; Kim, B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometallics 2003, 22, 3608 https://doi.org/10.1021/om030307h

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  3. A General Approach to Substituted Benzimidazoles and Benzoxazoles via Heterogeneous Palladium-Catalyzed Hydrogen-Transfer with Primary Amines pp.16154150, 2012, https://doi.org/10.1002/adsc.201200253
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  8. ChemInform Abstract: Ruthenium-Catalyzed Synthesis of Benzimidazoles from N-Alkyl-1,2-diaminobenzenes via Alkyl Group Transfer. vol.39, pp.43, 2008, https://doi.org/10.1002/chin.200843135
  9. Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous PdC catalysis pp.10990739, 2009, https://doi.org/10.1002/aoc.1596
  10. Rare-Earth Metal Chlorides as Efficient Catalysts for the Simple and Green Synthesis of 1,2-Disubstituted Benzimidazoles and 2-Substituted Benzothiazoles Under Ultrasound Irradiation vol.42, pp.3, 2008, https://doi.org/10.1080/00397911.2010.524337
  11. 1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates vol.85, pp.4, 2020, https://doi.org/10.1021/acs.joc.9b02714
  12. Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity vol.58, pp.1, 2021, https://doi.org/10.1002/jhet.4177