2-Imidazolone derivatives obtained as unexpected products throughout imidazole N-3-oxide rearrangement

摘要

3-Alkyl(aryl)-2,3-dihydro-1H-2-imidazolone derivatives as unexpected product of the reaction between ethyl 3-alkyl(aryl)amino-2-oximinobutanoate and methyl orthoformate is described. These imidazolones are generated by an intramolecular attack and a migration of N-3-oxide oxygen from the imidazole N-3-oxide intermediates. This proposed mechanism is supported by the results of theoretical studies (DFT).