Issue 17, 1997

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

Abstract

2-Unsubstituted isoxazol-5(4H )-ones and -5(2H )-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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 2659-2664

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

R. H. Prager, J. A. Smith, B. Weber and C. M. Williams, J. Chem. Soc., Perkin Trans. 1, 1997, 2659 DOI: 10.1039/A700133I

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