Synthesis of Functionalized 3‐(1<i>H</i>‐Isochromen)‐chromones <i>via</i> Ag<sub>2</sub>O‐Catalyzed Cascade Cyclization Reaction of <i>o‐</i>Hydroxyarylenaminones with <i>o</i>‐Alkynylbenzaldehydes
Mingshuai Zhang, Zhuoyuan Liu, Longkun Chen, Donghan Liu, Yulin Sun, Zhangmengjie Chai, Xuebing Chen, Fuchao Yu
Abstract
Abstract A silver‐catalyzed protocol for the synthesis of 3‐(1 H ‐isochromen)‐chromones is described. The method involves an initial 6‐endo‐dig cyclization of o ‐alkynylbenzaldehydes and domino C−H alkylation and chromone annulation of the o ‐hydroxyarylenaminones, which enables the installation of 1 H ‐isochromen and chromone in a single structure. This synthetic strategy is advantageous for the excellent regioselectivity, step economy, concise one‐pot methodology, gram‐scale synthesis, as well as high bond‐forming efficiency. magnified image
Topics & Concepts
ChromoneChemistryAnnulationRegioselectivityCatalysisDominoCascade reactionAlkylationCombinatorial chemistryCascadeStereochemistryOrganic chemistryMedicinal chemistryChromatographySynthesis of Organic CompoundsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions