Canadian Journal of Chemistry

Studies in isoxazole chemistry. III. The preparation and lithiation of 3, 5-disubstituted isoxazoles

RG Micetich, CG Chin

Index: Micetich,R.G.; Chin,C.G. Canadian Journal of Chemistry, 1970 , vol. 48, p. 1371 - 1376

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Citation Number: 27

Abstract

3-Arylisoxazol-5-ones and 5-arylisoxazol-3-ones were prepared and converted to the N- methyl and O-methyl derivatives by reaction with diazomethane. The halogen in 3-phenyl-5- chloroisoxazole was replaced by several alkoxy and thioalkoxy groups. The 3, 5- disubstituted isoxazoles thus obtained reacted with n-butyllithium to form the 4-lithio derivatives, as shown by conversion to 4-carboxylic acids and 4-iodocompounds. 3- ...