Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.
School of Pharmaceutical Sciences and Innovative Drug Research Centre, Chongqing University , 55 Daxuecheng South Road, Shapingba, Chongqing 401331, China.
J Org Chem. 2017 Dec 1;82(23):12682-12690. doi: 10.1021/acs.joc.7b02491. Epub 2017 Oct 26.
Treatment of enamino esters with TBHP (t-butylhydroperoxide) and TBAI (t-butylammonium iodide) in HFIP (hexafluoroisopropanol) was found to afford a variety of substituted pyrrolin-4-one compounds. This metal-free oxidative cascade reaction consists of the key steps of coupling of two radical intermediates, an intramolecular ring closure, and an exclusive 1,2-aryl radical migration. Upon treatment with a base, the obtained pyrrolin-4-ones could be converted to the highly substituted pyrrole compounds.
用 TBHP（叔丁基过氧化氢）和 TBAI（叔丁基碘化铵）处理 enamino 酯在 HFIP（六氟异丙醇）中发现可以得到各种取代的吡咯啉-4-酮化合物。这种无金属的氧化级联反应包括两个自由基中间体的偶联、分子内环化和独特的 1,2-芳基自由基迁移等关键步骤。用碱处理后，得到的吡咯啉-4-酮可以转化为高取代的吡咯化合物。
