含氮分子的选择性杂芳基 N-氧化。
Selective Heteroaryl N-Oxidation of Amine-Containing Molecules.
机构信息
Department of Chemistry , University of Virginia , Charlottesville , Virginia 22904-4319 , United States.
出版信息
Org Lett. 2018 Apr 6;20(7):2011-2014. doi: 10.1021/acs.orglett.8b00558. Epub 2018 Mar 16.
Abstract
The first examples of nonenzymatic N-oxidation of heteroarenes in the presence of amines are reported. Pyridine, quinoline, and isoquinoline N-oxides are selectively formed in the presence of more reactive aliphatic and alicyclic amines by use of an in situ protonation strategy and an iminium salt organocatalyst. Application to late-stage functionalization that mimics phase 1 metabolism of small-molecule drugs is also demonstrated.
摘要
首次报道了在胺存在下杂芳烃的非酶促 N-氧化的实例。通过原位质子化策略和亚胺盐有机催化剂的使用，在更具反应性的脂肪族和脂环族胺存在下，选择性地形成吡啶、喹啉和异喹啉 N-氧化物。还展示了模拟小分子药物一期代谢的后期官能化应用。
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