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Interconversion of 3‐Acylaminobenzisoxazoles and 3‐(2‐Hydroxyphenyl)‐1,2,4‐oxadiazoles
Author(s) -
Harsányi Kálmán
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100613
Subject(s) - chemistry , triethylamine , carboxylate , adduct , hydrolysis , substituent , medicinal chemistry , base (topology) , reagent , alkaline hydrolysis , alcohol , hydroxide , yield (engineering) , ion , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy
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).