期刊
TETRAHEDRON
卷 70, 期 21, 页码 3407-3412出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.03.082
关键词
Peptidomimetics; Tautomerism; alpha-Amino nitriles; Imidazolidine-2-one derivatives; Hydantoin derivatives
资金
- Spanish Ministerio de Ciencia e Innovacion [SAF2009-09323, SAF2012-32209]
- Ministerio de Educacion y Ciencia
- CSIC
The potential of alpha-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 alpha-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 C-5 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. (C) 2014 Elsevier Ltd. All rights reserved.
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