Interconversion of 3‐Acylaminobenzisoxazoles and 3‐(2‐Hydroxyphenyl)‐1,2,4‐oxadiazoles
- 1 December 1973
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 10 (6), 957-961
- https://doi.org/10.1002/jhet.5570100613
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).This publication has 7 references indexed in Scilit:
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