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Synthesis 1988; 1988(3): 203-207
DOI: 10.1055/s-1988-27512
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The Reactions of 3-Unsubstituted Isoxazolium Salts with 1,2-Dinucleophiles. Synthesis of 4-Functionalized 3-Aminoisoxazoles and 3-Aminopyrazoles

A. Alberola* , L. F. Antolín, P. Cuadrado, A. M. González, M. A. Laguna, F. J. Pulido
  • *Departamento de Química Orgánica, Universidad de Valladolid, E-47011-Valladolid, Spain
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Publikationsdatum:
20. August 2002 (online)

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The reaction of 3-unsubstituted isoxazolium salts with 1,2-dinucleophiles (hydroxylamine, hydrazine, methylhydrazine, phenylhydrazine, 4-nitrophenylhydrazine, semicarbazide) in boiling ethanol, affords 4-functionalized 3-alkylaminoisoxazoles and 3-alkylaminopyrazoles in high yields. The procedure is quite general, thus providing a new method for the synthesis of 3-aminoazoles with potential biological activity. Mechanistic pathways for these transformations are proposed.