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

ISSN: 1570-1786
E-ISSN: 1875-6255

2-Imidazolone Derivatives Obtained as Unexpected Products Throughout Imidazole N3-Oxide Rearrangement (Supplementary Material Available)
Authors: H. Cerecetto¹, A. Gerpe², M. Gonzalez³, O. E. Piro⁴ and E. E. Castellano⁵
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¹ Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Igua 4225, 11400 Montevideo, Uruguay; ² Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Igua 4225, 11400 Montevideo, Uruguay; ³ Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Igua 4225, 11400 Montevideo, Uruguay; ⁴ Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Igua 4225, 11400 Montevideo, Uruguay; ⁵ Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Igua 4225, 11400 Montevideo, Uruguay;
Source: Letters in Organic Chemistry, Volume 2, Issue 6, Sep 2005, p. 501 - 506
DOI: https://doi.org/10.2174/1570178054640778
- Available online: 01 Sep 2005

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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2005-09-01

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Article Type: Review Article

Keyword(s): imidazolone; n-oxide migration

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

Abstract

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