119392-86-8Relevant articles and documents
Ring Transformation of 1,2-Disubstituted 4(1H)-Quinazolone Oximes to 3,5-Disubstituted 1,2,4-Oxadiazoles
Korbonits, Dezsoe,Kanzel-Szvoboda, Ida,Goenczi, Csaba,Simon, Kalman,Kolonits, Pal
, p. 1107 - 1112 (2007/10/02)
In basic media O-benzoyl- and O-acetyl-2-benzylaminobenzamide oxime (8b, c) give 5-substituted 3-(2-benzylaminophenyl)-1,2,4-oxadiazoles (9a, b), while on heating in pure water 2-amino-1-benzylbenzimidazole (10) is formed.Reaction of 2-(N-acylbenzylamino)benzonitrile (12) with hydroxylamine, or treatment of O-acyl-2-(N-benzoylbenzylamino)benzamide oximes (8f, g) with acid give the novel 1,2-disubstituted 4(1H)-quinazolone oximes 13, which isomerize on heating with alkali by an ANRORC mechanism to the 1,2,4-oxadiazoles 9a, b. - Keywords: ANRORC mechanism; 1,2,4-Oxadiazoles; 4(1H)-Quinazolone oximes