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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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Kálmán Harsányi (1973) studied this question.
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