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Título

Chameleonic reactivity of α-amino nitrile-derived ureas. Synthesis of highly functionalized imidazolidin-2-one and imidazolidine-2,4-dione derivatives

Autor Ventosa-Andrés, Pilar ; González-Verdejo, Juan A.; García-López, M. Teresa ; Herranz, Rosario
Palabras clave Peptidomimetics
Tautomerism
α-Amino nitriles
Imidazolidine-2-one derivatives
Fecha de publicación 2014
EditorElsevier
Citación Tetrahedron 70: 3407- 3412 (2014)
ResumenThe potential of α-amino nitrile-derived ureas for the synthesis of imidazolidin-2-one derivatives has been studied in the context of a medicinal chemistry project focused on the search of antagonists of the thrombin receptor PAR1. In this study α-amino nitrile-derived ureas have shown chameleonic reactivity. Thus, under neutral, basic or mild acid media they cyclize to 4-iminoimidazolidin-2-one derivatives, which tautomerize to 4-amino-2,3-dihydro- 1H-imidazol-2-ones. This tautomerism triggers epimerization at the C5 of the imidazolidine ring, as well as its oxidation. However, they give stable highly functionalized hydantoin derivatives under strong acid media, by a no-epimerizing two-step hydrolysis.
URI http://hdl.handle.net/10261/97462
DOI10.1016/j.tet.2014.03.082
Identificadoresdoi: 10.1016/j.tet.2014.03.082
issn: 0040-4020
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