General Synthesis of Fully Substituted 4-Aminooxazoles from Amides and 1,4,2-Dioxazol-5-ones Based on Amide Activation and Umpolung Process.
General Synthesis of Fully Substituted 4-Aminooxazoles from Amides and 1,4,2-Dioxazol-5-ones Based on Amide Activation and Umpolung Process.
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DOI：
10.1021/acs.joc.0c02015
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发表时间：
2020-12
期刊：
影响因子：
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通讯作者：
Yunxiang Weng;L. Min;L. Shan;Hongchen Li;Xinyan Wang-;Yuefei Hu
中科院分区：
文献类型：
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作者：
Yunxiang Weng;L. Min;L. Shan;Hongchen Li;Xinyan Wang-;Yuefei Hu
基于酰胺活化和Umpolung反应策略，发展了一种通用、高效的全取代4-氨基二恶唑的合成方法。在该方法中，1，4，2-二恶唑-5-酮作为一种罕见的带有亲核N原子的极化试剂被引入，该试剂可以与活化剂Tf 2 O很好地一起使用。由于1，4，2-二恶唑-5-酮作为一种非极性试剂、底物和弱碱发挥着三重作用，该方法在极其方便的条件下进行得很顺利。
A general and efficient synthesis of fully substituted 4-aminodixazoles was developed based on the strategies of amide activation and umpolung reaction. In this method, 1,4,2-dioxazol-5-ones were introduced as a rare type of umpolung reagent bearing a nucleophilic N-atom that could be used well together with the activating agent Tf2O. Because 1,4,2-dioxazol-5-ones played triple roles as an umpolung reagent, a substrate, and a weak base, the method proceeded smoothly under extremely convenient conditions.