2-Imidazolone Derivatives Obtained as Unexpected Products Throughout Imidazole N3-Oxide Rearrangement (Supplementary Material Available)

H.      Cerecetto; A.      Gerpe; M.      Gonzalez; O.   E.   Piro; E.   E.   Castellano

doi:10.2174/1570178054640778

Abstract

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 N3-oxide oxygen from the imidazole N3-oxide intermediates. This proposed mechanism is supported by the results of theoretical studies (DFT).

Keywords: imidazolone, n-oxide migration

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Letters in Organic Chemistry

Title: 2-Imidazolone Derivatives Obtained as Unexpected Products Throughout Imidazole N3-Oxide Rearrangement (Supplementary Material Available)

Volume: 2 Issue: 6

Author(s): H. Cerecetto, A. Gerpe, M. Gonzalez, O. E. Piro and E. E. Castellano

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Keywords: imidazolone, n-oxide migration

Abstract: 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 N3-oxide oxygen from the imidazole N3-oxide intermediates. This proposed mechanism is supported by the results of theoretical studies (DFT).

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Cerecetto H., Gerpe A., Gonzalez M., Piro E. O. and Castellano E. E., 2-Imidazolone Derivatives Obtained as Unexpected Products Throughout Imidazole N3-Oxide Rearrangement (Supplementary Material Available), Letters in Organic Chemistry 2005; 2 (6) . https://dx.doi.org/10.2174/1570178054640778