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Formation of α‐(acylamino)butyramide oximes from 5‐substituted 3‐(1‐aminopropyl)‐1,2,4‐oxadiazoles: An astonishing hydrolytic transformation
Author(s) -
Bakó Erzsébet M.,
Horváth Károly,
Pálosi Endre,
Korbonits Dezső
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210419
Subject(s) - chemistry , nucleophile , sodium ethoxide , oxime , hydroxylamine , hydrolysis , medicinal chemistry , sodium hydroxide , organic chemistry , ethanol , catalysis
α‐Aminobutyramide oxime ( 6 ), obtained from α‐aminobutyronitrile ( 5 ) with hydroxylamine, reacted with esters in the presence of sodium ethoxide to furnish 5‐substituted 3‐(1‐aminopropyl)‐1,2,4‐oxadiazoles 7 . α‐(Acylamino)butyramide oximes 8 were formed from the compounds 7 by the action of dilute aqueous sodium hydroxide at ambient temperature. This astonishing reaction presumably proceeds by nucleophilic ring fission.