Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of <i>N</i>‐Acyl Hydrazones with <i>α</i>‐Substituted Vinyl Azides
Biao Nie, Wanqing Wu, Wei Zeng, Qingyun Ren, Ji Zhang, Ying‐Jun Zhang, Huanfeng Jiang
Abstract
Abstract A palladium‐catalyzed cyclization of N ‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α ‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using hydrazone as directing group. magnified image
Topics & Concepts
ChemistryIsoquinolinePalladiumHydrazoneCatalysisAzideBond cleavageTriple bondCleavage (geology)Medicinal chemistryCombinatorial chemistryDouble bondPolymer chemistryOrganic chemistryFracture (geology)Geotechnical engineeringEngineeringCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions