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DOI: 10.1039/A700133I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2659-2664

Chemistry of 5-oxodihydroisoxazoles. Part 17.1 Acylation of 5-oxodihydroisoxazoles

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Rolf H. Prager, Jason A. Smith, Ben Weber and Craig M. Williams

Abstract

2-Unsubstituted isoxazol-5(4H[hair space])-ones and -5(2H[hair space])-ones may be acylated by acid chlorides, anhydrides or carboxylic acids in the presence of carbodiimides, to give O- and N-acylated products. The solvent, the presence of base and the temperature are found to alter the product ratios dramatically, but the substituents present at C-3 have the greatest effect. Aliphatic acid anhydrides and chlorides generally react at nitrogen, but aroyl halides give significant proportions of O-acylated products. Limited success in converting O-aroyl to N-aroyl isoxazolones is reported.

References

  1. Part 16. R. H. Prager and C. M. Williams, Aust. J. Chem., 1996, 49, 1315 Search PubMed and references therein to earlier parts.
  2. R. H. Prager and Y. Singh, Tetrahedron, 1993, 49, 8147 CrossRef CAS.
  3. K. H. Ang and R. H. Prager, Tetrahedron Lett., 1992, 33, 2845 CrossRef CAS.
  4. K. H. Ang, R. H. Prager and C. M. Williams, Aust. J. Chem., 1995, 48, 567 CAS; K. H. Ang and R. H. Prager, Aust. J. Chem., 1993, 46, 477 CAS; K. H. Ang and R. H. Prager, Tetrahedron, 1992, 48, 9073 CrossRef CAS.
  5. R. H. Prager, Y. Singh and B. Weber, Aust. J. Chem., 1994, 47, 1249 CAS.
  6. K. H. Ang, R. H. Prager, J. A. Smith, B. Weber and C. M. Williams, Tetrahedron Lett., 1996, 37, 675 CrossRef CAS.
  7. P. Rabe, Ber. Dtsch. Chem. Ges., 1897, 30, 1614 Search PubMed.
  8. T. Posner, Ber. Dtsch. Chem. Ges., 1906, 39, 3515 CAS.
  9. F. Korte and K. Storiko, Ber. Dtsch. Chem. Ges., 1961, 94, 1956 CAS.
  10. E. P. Kohler and A. H. Blatt, J. Am. Chem. Soc., 1928, 50, 504 CrossRef CAS.
  11. I. F. Eckhard, K. Lehtonen, T. Staub and L. A. Summers, Aust. J. Chem., 1973, 26, 2705 CAS.
  12. V. P. Kurkov, US. P 4,504,486/ 1985(Chem. Abstr., 1985, 103, 54064n) Search PubMed.
  13. J. March, Advanced Organic Chemistry, J. Wiley, New York, 4th edn., 1992, vol. 1, p. 365 Search PubMed.
  14. T. H. Black, Org. Prep. Proced. Int., 1989, 21, 179 CAS.
  15. F. Effenberger, A. O. Muck and E. Bessey, Chem. Ber., 1980, 113, 2086 CAS.
  16. G. Speroni, Gazz. Chim. Ital., 1952, 82, 691 CAS.
  17. E. J. Bourne, M. Stacey, J. C. Tatlow and R. Worrall, J. Chem. Soc., 1954, 2006 RSC.
  18. E. L. Williams, Tetrahedron Lett., 1992, 33, 1033 CrossRef CAS.
  19. G. Speroni and E. Giachetti, Gazz. Chim. Ital., 1953, 83, 192 CAS.
  20. S. Ruhemann and R. S. Morrell, J. Chem. Soc., 1892, 61, 791 Search PubMed.
  21. H. Ulrich, J. N. Tilley and A. A. Sayigh, J. Org. Chem., 1962, 27, 2160 CAS.
  22. N. Bregant and I. Perina, J. Heterocycl. Chem., 1978, 15, 1145 CAS.
  23. A. R. Katritzky, P. Barczynski, D. L. Ostercamp and T. I. Yousaf, J. Org. Chem., 1986, 51, 4037 CrossRef CAS.
  24. D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon Press, Oxford, 3rd edn., 1988, vol. 1 Search PubMed.
  25. H. Rupe and B. Pieper, Helv. Chim. Acta, 1929, 12, 645.
  26. A. Haller and E. Bauer, C. R. Acad. Sci. Paris, 1911, 152, 1446 Search PubMed.
  27. R. Jacquier, C. Petrus, F. Petrus and J. Verducci, Bull. Soc. Chim. Fr., 1970, 7, 2690.
  28. G. Adembri and P. Tedeschi, Boll. Sci. Fac. Chim. Ind. Bologna., 1965, 23, 203 (Chem. Abstr., 1965, 63, 1324h) Search PubMed.
  29. L. Claisen and E. Haase, Justus Liebigs Ann. Chem., 1897, 297, 81.
  30. Y. Singh and R. H. Prager, Aust. J. Chem., 1992, 45, 1811 CAS.
  31. A. R. Katritzky, S. Oksne and A. J. Boulton, Tetrahedron, 1962, 18, 777 CrossRef CAS.
  32. R. Breslow, T. Eicher, A. Krebs, R. A. Peterson and J. Posner, J. Am. Chem. Soc., 1965, 87, 1320 CrossRef CAS.
  33. F. De Sarlo, G. Dini and P. Lacrimini, J. Chem. Soc. (C), 1971, 86 RSC.
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