2- Imidazolone Derivatives Obtained as Unexpected Products Throughout Imidazole N3- oxide Rearrangement

H. CERECETTO; A. GERPE; M. GONZALEZ; OSCAR ENRIQUE PIRO; CASTELLANO, EE

Letter in Organic Chemistry of Bentham

Bentham Science Publishers

Año: 2005 vol. 2 p. 501 - 506

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).