Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation
Shaojing Jin, Lele Wang, Huabin Han, Xiong‐Li Liu, Zhanwei Bu, Qilin Wang
Abstract
Reported herein is an unexpected construction of functionalized π-extended indolizine polycycles through a one-pot two-step cascade process comprising the base-promoted dearomative [3+2] cycloaddition of quinilinium salts and 3-alkenyl oxindoles, followed by a DDQ-mediated oxidative decarbonylation. Moreover, we could achieve the substrate-controlled diverse synthesis of structurally strained cyclopropane spirooxindole by using pyridinium salts as starting materials.
Topics & Concepts
DecarbonylationIndolizineCycloadditionChemistryOxidative phosphorylationCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisBiochemistrySynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsSynthesis and Characterization of Pyrroles