Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[<i>c</i>]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes
Ming Bao, Xiongda Xie, Wenhao Hu, Xinfang Xu
Abstract
Abstract A gold‐catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4‐iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6‐ endo‐dig diazo‐yne carbocyclization to form the endocyclic vinyl carbene species from corresponding alkyne‐tethered diazo compounds, followed by electrophilic addition/N−O bond cleavage/aromatization sequence with benzo[ c ]isoxazoles, which features a C=N bond formation process. In addition, the resulting products could be converted into multi‐substituted 2‐naphthol derivatives in high yields. magnified image
Topics & Concepts
ChemistryDiazoAlkyneCarbeneTriple bondBond cleavageAromatizationCatalysisElectrophileMedicinal chemistryCyclopropanationStereochemistryCombinatorial chemistryDouble bondOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods