Advertisement

Chemistry of Heterocyclic Compounds

, Volume 42, Issue 7, pp 872–874 | Cite as

Selective hydrogenolysis of benzyl-protected 1-hydroxy-3-hydroxyimino-2-pyrrolidinones

  • M. Katkevichs
  • E. Korchagova
  • T. Ivanova
  • V. Slavinska
  • E. Lukevics
Article

Abstract

On hydrogenolysis of 1-benzyloxy-3-benzyloxyimino-2-pyrrolidinones in the presence of 10% Pd/C selective removal occurs of the O-benzyl (Bn) protection of the hydroxamic acid, with retention of the double bond and benzyl protection of the oxime group. The yields of reaction products were 66–98%.

Keywords

α-oxyiminohydroxamic acids 2-pyrrolidinone derivatives hydrogenolysis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M.-C. Fournie-Zaluski, A. Coulaud, R. Bouboutou, P. Chaillet, J. Devin, G. Waksman, J. Costentin, and B. P. Roques, J. Med. Chem., 28, 1158 (1985).CrossRefGoogle Scholar
  2. 2.
    G. Kottirsch, G. Koch, R. Feifel, and U. Neumann, J. Med. Chem., 45, 2289 (2002).CrossRefGoogle Scholar
  3. 3.
    M. R. Gowravaram, B. E. Tomczuk, J. S. Jonson, D. Delecki, E. R. Cook, A. K. Ghose, A. M. Mathiowetz, J. C. Spurlino, B. Rubin, D. L. Smith, T. Pulvino, and R. C. Wahl, J. Med. Chem., 38, 2570 (1995).CrossRefGoogle Scholar
  4. 4.
    A. Volonterio, S. Bellosta, P. Bravo, M. Canavesi, E. Corradi, S. V. Meille, M. Monetti, N. Moussier, and M. Zanda, Eur. J. Org. Chem., 3, 428 (2002).CrossRefGoogle Scholar
  5. 5.
    A. Volonterio, P. Bravo, and M. Zanda, Tetrahedron Lett., 42, 3141 (2001).CrossRefGoogle Scholar
  6. 6.
    P. Cozzi, A. Giordani, M. Menichincheri, A. Pillan, V. Pinciroli, A. Rossi, R. Tonani, D. Volpi, M. Tamburin, R. Ferrario, D. Fusar, and P. Salvati, J. Med. Chem., 37, 3588 (1994).CrossRefGoogle Scholar
  7. 7.
    W. Yao, M. Chao, Z. R. Wasserman, R. Q. Liu, M. B. Covington, R. Newton, D. Christ, R. R. Wexler, and C. P. Decicco, Bioorg. Med. Chem. Lett., 12, 101 (2002).CrossRefGoogle Scholar
  8. 8.
    M. Katkevich, E. Korchagova, T. Ivanova, V. Slavinska, and E. Lukevics, Khim. Geterotsikl. Soedin., 860 (2004) [Chem. Heterocycl. Comp., 40, 734 (2004)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • M. Katkevichs
    • 1
  • E. Korchagova
    • 1
  • T. Ivanova
    • 1
  • V. Slavinska
    • 1
  • E. Lukevics
    • 1
  1. 1.Latvian Institute of Organic SynthesisRiga

Personalised recommendations