Synthesis of Indolizines <i>via</i> Tf<sub>2</sub>O-Mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/Thioalcohols
Changyuan Zhang, Wei Wang, Xuncheng Zhu, Lulu Chen, Hejiang Luo, Mengping Guo, Dan Liu, Fan Liu, Huisheng Zhang, Qi Li, Jianping Lin
Abstract
A cost-effective, highly regioselective and metal-free version for the synthesis of indolizine derivatives by means of Tf 2 O-mediated cascade reaction of pyridyl-enaminones and thiophenols/thioalcohols under mild reaction conditions has been reported. Diverse electron-rich indolizine derivatives could be obtained in up to 94% yield via the selective 1,4-addition of vinyl iminium triflate tandem cyclization/aromatization, which allowed the simultaneous construction of C–N and C–S/and one example of C–Se bonds.
Topics & Concepts
IndolizineChemistryCascade reactionIminiumTandemRegioselectivityYield (engineering)Combinatorial chemistryTrifluoromethanesulfonateCascadeAromatizationReaction conditionsMedicinal chemistryOrganic chemistryCatalysisMaterials scienceChromatographyComposite materialMetallurgySynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsAdvanced Synthetic Organic Chemistry