Studies On The Transition-metal-catalyzed Cycloisomerization Reactions Of Benzo[d]isoxazoles

Benzo[d]isoxazole derivatives are a class of compounds that contain a five-membered heterocyclic ring structure.The compoundy can be used as key synthons to participate in many different types of reactions,which including multi-component reactions,nucleophilic reactions,electrophilic reactions,free radical reactions,and etc.,to generate various nitrogen-or oxygen-containing molecules.Based on the fruitful ring isomerization activity of benzo[d]isoxazole derivatives,this paper studies the ring-opening and rearrangement reactions of the materials under the conditions of transition-metal catalysis,thus to eggiciently and selectively construct various nitrogen-and oxygen-containing small organic compounds.This article is divided into three parts:In part 1,the various reactions in recent years with diazo compounds as carbene precursors are briefly summarized.The reactions of diazo compounds as metal carbene precursors are widely used in organic synthesis with raw materials.Seneral useful types of reactions had been developed,such as cyclopropanations,C-H bond insertions,and X-H（X=Si,O,N,S,P,etc.）bond insertion reactions,ylide reactions,1,2-migration reactions,and Wolff rearrangement reactions.In part 2,the Cu（acac）₂-catalyzed reactions ofα-diazoindole with benzo[d]isoxazole to give a series of 2,3-diiminoindolines were developed under mild conditions.The products can then be hydrogenated under Pd catalysis to be converted into 2,3-diaminoindoles in moderate yields.The reaction is well tolerant to various functional groups and has the characteristics of high atom economy.In part 3,the synergistic catalysis reaction of Au/Ag co-catalyzed nucleophilic addition reactions of propargyl alcohols with benzoisoxamines was reported.A wide range of（Z）-allyl alcohol compounds with absolute configurations were achieved in good yields.This reaction can be compatible with various electron withdrawing and electron donating groups,and at the same time,the reaction can be easily extended to the gram scale.