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

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• 作者：Pilar Ventosa-André ; s ; Juan A. Gonzá ; lez-Vera ; M. Teresa Garcí ; a-Ló ; pez ; Rosario Herranz ; ^{Rosario@iqm.csic.es" class="auth_mail}
• 关键词：Peptidomimetics ; Tautomerism ; 伪-Amino nitriles ; Imidazolidine-2-one derivatives ; Hydantoin derivatives
• 刊名：Tetrahedron
• 出版年：27 May, 2014
• 年：2014
• 卷：70
• 期：21
• 页码：3407-3412
• 全文大小：607 K

文摘

The potential of 伪-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 伪-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.