Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN<sub>3</sub>
Yu‐Fei Song, Zhaolin Quan, Zhengkai Chen, Xiao‐Feng Wu
Abstract
A facile and straightforward approach for the synthesis of fused quinoxalinones via palladium-catalyzed cascade carbonylative cyclization of 2-heteroaryl iodobenzene and NaN 3 has been achieved. The transformation might undergo cascade carbonylation, formation of acyl azide, a Curtius rearrangement, and an intramolecular cyclization sequence. The obtained heterocycle products can be easily transformed into other structurally diverse valuable compounds, which demonstrates the synthetic utility of the developed protocol.
Topics & Concepts
ChemistryIodobenzeneCarbonylationPalladiumCombinatorial chemistryCurtius rearrangementCascadeAzideIntramolecular forceCatalysisStereochemistryOrganic chemistryChromatographyCarbon monoxideSynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms