Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Isoxazolone Derivatives from (Chlorocarbonyl)phenyl Ketene with Benzhydroxamic Acids

  • Nejadshafiee, Vajihe (Department of Chemistry, Shahid Bahonar University of Kerman) ;
  • Saidi, Kazem (Department of Chemistry, Shahid Bahonar University of Kerman) ;
  • Abaszadeh, Mehdi (Department of Chemistry, Shahid Bahonar University of Kerman)
  • Received : 2011.07.30
  • Accepted : 2011.09.26
  • Published : 2011.12.20
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Abstract

The reaction of (chlorocarbonyl)phenyl ketene, with readily available benzhydroxamic acid derivatives, such as benzhydroxamic acid, 4-chlorobenzhydroxamic acid, 3-nitrobenzhydroxamic acid, 4-methylbenzhydroxamic acid, N-hydroxy-3-oxo-3-phenylpropionamide, N-hydroxy-2-phenylacetamide, affords isoxazolone derivatives in high yields in a one step procedure. The formation of the products proceeds by a mechanism, that involves replacement of chlorine of the ketene, by benzhydroxamic acids, followed by rapid ring closure of this intermediate to form isoxazolone derivatives.

Keywords

References

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