View PDF Version
 
DOI: 10.1039/A905519C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 3265-3268

Phenylation of pyrimidinones using diphenyliodonium salts

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

Stig André Jacobsen, Synne Rødbotten and Tore Benneche

Abstract

Pyrimidinones 1 have been phenylated under basic conditions using diphenyliodonium salts, and the effect of substituents on the yield and regiochemistry has been studied.

References

  1. A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH Publishers, Inc., New York, 1992 Search PubMed.
  2. (a) Ref. 1, pp. 207; (b) R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431 CrossRef CAS; (c) A. Varvoglis, Synthesis, 1984, 709 CrossRef CAS.
  3. (a) A. McKillop and R. J. Kobylecki, J. Org. Chem., 1974, 39, 2710 CrossRef CAS; (b) W.-Y. Chen and N. W. Gilman, J. Heterocycl. Chem., 1983, 20, 663 CAS; (c) S. Bátori and A. Messmer, J. Heterocycl. Chem., 1988, 25, 437 CAS.
  4. Direct O/N-arylation of amides has been achieved with aryl halides catalyzed by copper salts: B. Renger, Synthesis, 1985, 856 Search PubMed; A. Greiner, Synthesis, 1989, 312 CrossRef CAS with tetraphenylbismuth trifluoro-acetate: D. H. R. Barton, J.-P. Finet, W. B. Motherwell and C. Pichon, J. Chem. Soc., Perkin Trans. 1, 1987, 251 CrossRef CAS and with p-tolyllead triacetate: P. López-Alavardo, C. Avendaño and J. C. Menéndez, Tetrahedron Lett., 1992, 33, 6875 Search PubMed.
  5. (a) D. J. Brown and T.-C. Lee, Aust. J. Chem., 1968, 21, 243 CAS; (b) C. Kashima, A. Katoh, Y. Yokota and Y. Omote, Synthesis, 1983, 151 CrossRef; (c) J. Solberg, PhD Thesis, University of Oslo, 1988 Search PubMed.
  6. D. J. Brown, The Pyrimidines, Supplement II, Wiley & Sons, New York, 1985, p. 205 and references therein Search PubMed.
  7. A. N. Nesmeyanov, L. G. Makarova and T. P. Tolstaya, Tetrahedron, 1957, 145 CrossRef CAS.
  8. D. D. Perrin, B. Dempsey and E. P. Serjeant, pKa Prediction of Organic Acids and Bases, Chapman and Hall, London, 1981 Search PubMed.
  9. A. Albert and J. N. Phillips, J. Chem. Soc., 1956, 1294 RSC.
  10. D. J. Brown, The Pyrimidines, Wiley & Sons, New York, 1962, Table XVI, pp. 472 Search PubMed.
  11. D. J. Brown, The Pyrimidines, Supplement I, Wiley & Sons, New York, 1970, Table XVI, pp. 369 Search PubMed.
  12. M. F. Beringer, A. Brierley, M. Drexler, E. M. Grindler and C. C. Lumpkin, J. Am. Chem. Soc., 1953, 75, 2705 CrossRef CAS.
  13. J. L. Dektar and N. P. Hacker, J. Org. Chem., 1990, 55, 639 CrossRef CAS.
  14. D. G. Crosby and R. V. Berthold, J. Org. Chem., 1960, 25, 1916 CrossRef CAS.
  15. W. Franke and R. Kraft, Chem. Ber., 1953, 86, 797 CAS.
  16. G. E. Hilbert and T. B. Johnson, J. Am. Chem. Soc., 1930, 52, 2001 CrossRef CAS.
  17. M. Prystas, Collect. Czech. Chem. Commun., 1975, 40, 1786 CAS.
  18. M. L. Falck-Pedersen, T. Benneche and K. Undheim, Acta Chem. Scand., 1993, 47, 72 CAS.
  19. W. Szar and D. Shugar, Acta Biochim. Pol., 1966, 13, 177 Search PubMed.
  20. Z. Budésinsky, V. Bydzovsky, J. Kopecky, A. Sváb and J. Vavrina, Cesk. Farm., 1961, 10, 241 Search PubMed.
  21. Z. Budésinsky, J. Prikryl and E. Svátek, Collect. Czech. Chem. Commun., 1964, 29, 2980 CAS.
  22. Z. Budésinsky, J. Prikryl and E. Svátek, Collect. Czech. Chem. Commun., 1967, 32, 1637 CAS.
  23. A. Novácek and M. Lisserová, Collect. Czech. Chem. Commun., 1968, 33, 1003 CAS.
  24. T. Nishio, K. Katahira and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1981, 943 RSC.
  25. M. R. Atkinson, M. J. Maguire, R. K. Ralph, G. Shaw and R. N. Warrener, J. Chem. Soc., 1957, 2363 RSC.
  26. Y. F. Shealy and C. A. O'Dell, J. Heterocycl. Chem., 1976, 13, 1041 CAS.
  27. T. Joijima and S. Tamura, Agric. Biol. Chem., 1966, 30, 896.