Institute of Organic Chemistry, Faculty of Chemistry, University of Vienna , Währinger Straße 38, 1090 Vienna, Austria.
Institute of Theoretical Chemistry, Faculty of Chemistry, University of Vienna , Währinger Straße 17, 1090 Vienna, Austria.
Org Lett. 2017 Jul 21;19(14):3815-3818. doi: 10.1021/acs.orglett.7b01678. Epub 2017 Jul 13.
The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-position of amides as well as a mechanistically intriguing sequence that results in sulfonyl migration from nitrogen to carbon. Quantum-chemical mechanistic analysis sheds light on the intricacies of the process.
报道了通过三氟甲磺酸酐介导的酰胺活化作用，从α-芳酰胺和α-氨基酰胺制备取代的氨基恶唑和氨基咪唑。这些反应通过亚硝鎓盐促进酰胺α-位的反转以及导致磺酰基从氮迁移到碳的引人入胜的反应历程进行。量子化学机理分析揭示了该过程的复杂性。
Zotero 插件
