Facilitation of displacements at the 6-position of purines by the use of 1,4-diazabicyclo[2.2.2]octane as leaving group

(Note: The full text of this document is currently only available in the PDF Version )

Nicola K. Lembicz, Sharon Grant, William Clegg, Roger J. Griffin, Sarah L. Heath and Bernard T. Golding


Abstract

Reactions of 6-chloropurines with 1,4-diazabicyclo[2.2.2]octane (DABCO) give the corresponding ‘DABCO-purines’ 1a–d, which undergo facile displacement reactions with alkoxides in dimethyl sulfoxide to afford 6-oxy-substituted purines.


References

  1. A. E. Pegg, M. E. Dolan and R. C. Moschel, Prog. Nucleic Acid Res. Mol. Biol., 1995, 51, 162 Search PubMed.
  2. M. Y. Chae, M. G. McDougall, M. E. Dolan, K. Swenn, A. E. Pegg and R. C. Moschel, J. Med. Chem., 1994, 37, 342 CrossRef CAS.
  3. T. B. H. McMurry, R. S. McElhinney, J. McCormick, R. H. Elder, J. Kelly, G. P. Margison, J. A. Rafferty, A. J. Watson and M. A. Willington, Int. Pat. Appl., WO 94/29312 Search PubMed.
  4. C. Arris, C. Bleasdale, A. H. Calvert, N. J. Curtin, C. Dalby, B. T. Golding, R. J. Griffin, J. M. Lunn, G. N. Major and D. R. Newell, Anti-cancer Drug Des., 1994, 9, 401 Search PubMed.
  5. L. R. Lewis, F. H. Schneider and R. K. Robins, J. Org. Chem., 1961, 26, 3837 CrossRef CAS.
  6. J. Kiburis and J. H. Lister, J. Chem. Soc. (C), 1971, 3942 RSC.
  7. B. L. Gaffney and R. A. Jones, Tetrahedron Lett., 1982, 23, 2253 CrossRef.
  8. M. Ashwell, C. Bleasdale, B. T. Golding and I. K. O'Neill, J. Chem. Soc., Chem. Commun., 1990, 955 RSC.
  9. J. Kiburis and J. H. Lister, J. Chem. Soc. (C), 1971, 1587 RSC.
  10. H. J. Koeners, A. J. de Kok, C. Romers and J. H. van Boom, Recl. J. R. Neth. Chem. Soc., 1980, 99, 355 Search PubMed.
  11. S. D. Ross, J. J. Bruno and R. C. Peterson, J. Am. Chem. Soc., 1963, 85, 3999 CrossRef CAS.
  12. J. R. Gandler, I. U. Setiarahardjo, C. Tufon and C. Chen, J. Org. Chem., 1992, 57, 4169 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.