Diethyl Azodicarboxylate-Promoted Oxidative [3 + 2] Cycloaddition for the Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolines
Ya‐Wen Xu, Jiankun Wang, Guangji Wang, Le Zhen
Abstract
A novel metal-free protocol for the effective and efficient construction of pyrrolo[2,1-a]isoquinolines via a diethyl azodicarboxylate (DEAD)-promoted oxidative [3 + 2] cycloaddition/aromatization tandem reaction is described. Instead of the reported two-component oxidation systems, DEAD, as the sole oxidant, could smoothly transfer the tertiary amines to azomethine ylides via oxidation-deprotonation tandem process. The reaction proceeded with a broad substrate scope, giving rise to products in moderate to good isolated yields.
Topics & Concepts
Diethyl azodicarboxylateCycloadditionAromatizationChemistryDeprotonationTandemSubstrate (aquarium)Oxidative phosphorylationCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisOceanographyBiochemistryMaterials scienceIonComposite materialGeologyTriphenylphosphineCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesOxidative Organic Chemistry Reactions