Phase-transfer-catalysed Preparation of N-Alkylated Trihydroxamic Acids†

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Pascal Hoffmann, Jean-Baptiste Doucet, Wenhao Li, Laurent Vergnes and Serge Labidalle


Abstract

We describe a synthetic route involving phase transfer catalysis leading to a series of tripodal N-alkylated hydroxamic acids as models of desferrioxamine; iron(III) exchange reactions between their iron complexes and EDTA were investigated.


References

  1. J. B. Neilands, Science, 1967, 156, 1443 CAS; R. J. Bergeron, Chem. Rev., 1984, 84, 587 CrossRef CAS.
  2. R. J. Bergeron, C. Z. Liu, J. S. McManis, M. X. B. Xia, S. E. Algee and J. Weigand, J. Med. Chem., 1994, 37, 1411 CrossRef CAS.
  3. C. Sappey, J. R. Boelaert, S. Legrand-Poels, C. Forceille, A. Favier and J. Piette, AIDS Res. Hum. Retroviruses, 1995, 11, 1049 CAS.
  4. (a) E. V. Dehmlow, Angew. Chem., Int. Ed. Engl., 1977, 16, 493 CrossRef; (b) for Michael addition via PTC, see for example: V. Dryanska, K. Popandova and C. Ivanov, Synth. Commun., 1987, 17, 211 Search PubMed; G. Bram, H. Galons, S. Labidalle, A. Loupy, M. Miocque, A. Petit, P. Pigeon and J. Sansoulet, Bull. Soc. Chim. Fr., 1989, 247 CAS; (c) for PTC N-alkylation, see for example: R. J. M. Nolte and D. J. Cram, J. Am. Chem. Soc., 1984, 106, 1416 Search PubMed; E. V. Dehmlow and Y. R. Rao, Synth. Commun., 1988, 18, 487 CrossRef CAS.
  5. G. R. Newkome, C. N. Moorefield and G. R. Baker, Aldrichim. Acta, 1992, 25, 31 Search PubMed.
  6. A. M. Lobo, M. M. Marques, S. Prabhakar and H. S. Rzepa, J. Org. Chem., 1987, 52, 2925 CrossRef CAS; R. J. Bergeron and J. S. McManis, Tetrahedron, 1990, 46, 5881 CrossRef CAS; J. M. Altenburger, C. Mioskowski, H. d'Orchymont, D. Schirlin, C. Schalk and C. Tarnus, Tetrahedron Lett., 1992, 33, 5055 CrossRef CAS; M. A. Staszak and C. W. Doecke, Tetrahedron Lett., 1994, 35, 6021 CrossRef CAS; J. Zhu, S. Robin, C. Goasdoué, A. Loupy and H. Galons, Synth. Commun., 1995, 25, 2515 CAS; S. S. Nikam, B. E. Kornberg, D. R. Johnson and A. M. Doherty, Tetrahedron Lett., 1995, 36, 197 CrossRef CAS.
  7. M. Akiyama, A. Katoh and T. Ogawa, J. Chem. Soc., Perkin Trans. 2, 1989, 1213 RSC.
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