Download PDF
Synthesis 1988; 1988(3): 203-207
DOI: 10.1055/s-1988-27512
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.