Interconversion of 3-Acylaminobenzisoxazoles and 3-(2-Hydroxyphenyl)-1,2,4-oxadiazoles |
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Authors: | K lm n Hars nyi |
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Affiliation: | Kálmán Harsányi |
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Abstract: | Interconversion of 3-(2-hydroxyphenyl)-1,2,4-oxadiazoles (1) and 3-acylaminobenzisoxazoles (2) was observed in the presence of base carboxylate anion, triethylamine, alkali hydroxide, alcoholate. With proton transferring reagents (carboxylate, triethylamine) the equilibrium 1?2 is dependent on the substituent R; with anionic reagents (hydroxy anion, ethoxyl anion) the less basic anion of 1 is preferred. Alcohol effects further transformation of this anion and the alcohol adduct anion (6) is subject both to hydrolysis and alcoholysis (7) to yield 3-amino-benzisoxazole (3). |
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