Advertisement

Russian Chemical Bulletin

, Volume 56, Issue 6, pp 1216–1226 | Cite as

Hydrogenation on palladium-containing granulated catalysts 3. Synthesis of aminobenzimidazoles by catalytic hydrogenation of dinitroanilines

  • V. V. Elkin
  • L. N. Tolkacheva
  • N. B. Chernysheva
  • I. B. Karmanova
  • L. D. Konyushkin
  • V. V. Semenov
Article

Abstract

Efficient hydrogenation of o-aminonitrobenzenes on palladium-containing granulated carbon catalysts in carboxylic acid solutions was accompanied by cyclization into aminobenzimidazoles. A simple hydrogenation reactor with a fixed gauze holding a reusable granulated catalyst was designed. Acylated and sulfonylated 4(7)-aminobenzimidazoles were obtained. In terms of electronic and geometrical parameters, they are close analogs of biologically active imidazo[1,5,4-e,f ][1,5]benzodiazepines.

Key words

hydrogenation aminobenzimidazoles o-aminonitrobenzenes dinitroanilines palladium-containing granulated catalysts 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    V. P. Kislyi, L. N. Tolkacheva, and V. V. Semenov, Zh. Org. Khim., 2002, 38, 290 [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].Google Scholar
  2. 2.
    L. Tatulian, P. Delmas, F. C. Abogadie, and D. A. Brown, J. Neurosci., 2001, 21, 5535.Google Scholar
  3. 3.
    G. Bhattacharya, J. Herman, D. Delfín, M. M. Salem, T. Barszcz, M. Mollet, G. Riccio, R. Brun, and K. A. Werbovetz, J. Med. Chem., 2004, 47, 1823.CrossRefGoogle Scholar
  4. 4.
    A. Marcos, C. Pedregal, and C. Avendano, Tetrahedron, 1991, 47, 7459.CrossRefGoogle Scholar
  5. 5.
    Z. Zhao, D. O. Arnaiz, B. Griedel, S. Sakata, J. L. Dallas, M. Whitlow, L. Trinh, J. Post, A. Liang, M. M. Morrissey, and K. J. Shaw, Bioorg. Med. Chem. Lett., 2000, 10, 963.CrossRefGoogle Scholar
  6. 6.
    N. H. Hauel, H. Nar, H. Priepke, U. Ries, J.-M. Stassen, and W. Wienen, J. Med. Chem., 2002, 45, 1757.CrossRefGoogle Scholar
  7. 7.
    J. A. McCauley, C. R. Theberge, J. J. Romano, S. B. Billings, and K. D. Anderson, J. Med. Chem., 2004, 47, 2089.CrossRefGoogle Scholar
  8. 8.
    L. F. Olguin, M. Jimenez-Estrada, E. Barzana, and A. Navarro-Ocana, Synlett, 2005, 2, 340.Google Scholar
  9. 9.
    I. G. Moores, R. K. Smalley, and H. Suschitzky, J. Fluorine Chem., 1982, 20, 573.CrossRefGoogle Scholar
  10. 10.
    H. Gilman and H. S. Broadbent, J. Am. Chem. Soc., 1948, 70, 2619.CrossRefGoogle Scholar
  11. 11.
    R. E. Lyle and J. L. LaMattia, J. Org. Chem., 1975, 40, 438.CrossRefGoogle Scholar
  12. 12.
    J. R. E. Hoover and A. R. Day, J. Am. Chem. Soc., 1955, 77, 4324.CrossRefGoogle Scholar
  13. 13.
    B. C. Platt and T. M. Sharp, J. Chem. Soc., 1948, 2129.Google Scholar
  14. 14.
    G. Kh. Khisamutdinov, V. L. Korolev, I. Z. Kondyukov, I. Sh. Abdrakhmanov, S. P. Smirnov, A. A. Fainzil’berg, and V. G. Dorokhov, Izv. Akad. Nauk, Ser. Khim., 1993, 152 [Russ. Chem. Bull., 1993, 42 (Engl. Transl.)].Google Scholar
  15. 15.
    L. N. Tolkacheva, V. P. Kislyi, S. Z. Taits, and V. V. Semenov, Zh. Org. Khim., 2002, 38, 170 [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].Google Scholar
  16. 16.
    W. Theilheimer, Synthetic Methods of Organic Chemistry, 1969, 23, 233.Google Scholar
  17. 17.
    K. Lindemann, J. Prakt. Chem., 1927, 259.Google Scholar
  18. 18.
    A. V. Vlaskina and V. P. Perevalov, Khim. Geterotsikl. Soedin., 2004, 620 [Chem. Heterocycl. Compd., 2004, 40 (Engl. Transl.)].Google Scholar
  19. 19.
    M. A. Phillips, J. Chem. Soc., 1930, 1409.Google Scholar
  20. 20.
    W. King Beer, J. Chem. Soc., 1946, 92.Google Scholar
  21. 21.
    M. N. Semenova, A. S. Kiselyov, and V. V. Semenov, BioTechniques, 2006, 40, 765.CrossRefGoogle Scholar
  22. 22.
    Organic Syntheses, New York-London, 1946–1952, 26–32.Google Scholar
  23. 23.
    L. S. Efros, Zh. Obshch. Khim., 1953, 23, 957 [J. Gen. Chem. USSR, 1953, 23 (Engl. Transl.)].Google Scholar
  24. 24.
    H. Salkowski, Ber., 1877, 10, 1693.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. V. Elkin
    • 1
  • L. N. Tolkacheva
    • 1
  • N. B. Chernysheva
    • 1
  • I. B. Karmanova
    • 1
  • L. D. Konyushkin
    • 1
  • V. V. Semenov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations