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Rhodium‐Catalyzed Cascade Reactions of Indoles with 4‐Hydroxy‐2‐Alkynoates for the Synthesis of Indole‐Fused Polyheterocycles

Xiaowei Wu, Pinyi Li, Yangbin Lu, Qiao Jin, Jingwei Zhao, Xiuwen Jia, Hangcheng Ni, Lichun Kong, Xiaoning Zhang, Fei Zhao

2020Advanced Synthesis & Catalysis38 citationsDOIOpen Access PDF

Abstract

Abstract Herein, an efficient and regioselective Rh(III)‐catalyzed [4+2] annulation/lactonization cascade of indoles with 4‐hydroxy‐2‐alkynoates at room temperature to access the furo[3′,4′:4,5]pyrimido[1,6‐ a ]indole‐1,5(3 H ,4 H )‐diones is described. This method features mild reaction conditions, operational simplicity, excellent regioselectivity, broad substrate scope with good functional group tolerance, and good to excellent yields. magnified image

Topics & Concepts

ChemistryRegioselectivityAnnulationIndole testCatalysisRhodiumCascadeSubstrate (aquarium)Combinatorial chemistryReaction conditionsFunctional groupOrganic chemistryStereochemistryMedicinal chemistryChromatographyPolymerGeologyOceanographyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions
Rhodium‐Catalyzed Cascade Reactions of Indoles with 4‐Hydroxy‐2‐Alkynoates for the Synthesis of Indole‐Fused Polyheterocycles | Litcius