Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

中文翻译：

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（2,2-二烷氧基乙基）脲的亲核环化/亲电取代：高度区域选择性访问新型4-（Het）芳基咪唑烷酮和苯并[d] [1,3]二氮杂吡啶酮

作为特别主题的一部分发表，酰胺键形成的最新进展

抽象

咪唑啉丁-2-酮和1,3-苯并二氮杂-2-酮骨架是许多生物活性化合物的结构基序。在本文中，我们报道了（2，2-二烷氧基乙基）脲的高度区域选择性酸催化的分子内亲核环化/分子间亲电取代反应序列。该反应得益于容易获得的起始原料，简单的后处理步骤，中等至高产率的目标化合物，并且可以方便地进入先前未知的4-（杂）芳基咪唑烷酮和5-（杂）芳基苯并二氮杂酮。还讨论了所提出的反应机理。