Construction Of Isoquinolinone And Thiazole Derivatives By Multi-component Reaction

Compared with traditional synthesis methods,multi-component reaction has the advantages of high economy,high synthesis efficiency and high flexibility,which has a very important application value in the fields of organic synthesis methodology and pharmaceutical chemistry.Nitrogen-containing heterocyclic compounds with isoquinolinone and thiazole skeletons have been widely used in natural products,drugs and functional materials.Although many methods have been reported for the synthesis of these two nitrogen-containing heterocyclic compounds,it is important to develop new efficient and green methods for the synthesis of polyfunctionalized isoquinolinone and thiazole derivatives.In this thesis,the multi-component reaction strategy was adopted to establish two rapid and efficient synthesis methods for the construction of selenethers isoquinolinone derivatives and thiazole derivatives.The specific research content includes two parts:(1)We realized the electrochemical reaction of regioselective oxidation/selenated N-alkyl isoquinoline salt to construct selenized isoquinolinone.The reaction uses potassium iodide as the electrolyte and cesium carbonate as the additive.In a constant current undivided electrolytic cell,N-alkylisoquinoline salt,disubstituted selenoether and oxygen are in a mixed solvent of acetonitrile and water.Through this sustainable and clean electrochemical system,a series of selenized isoquinolinone derivatives were synthesized.(2)We realized the synthesis of a variety of functionalized thiazole compounds by monovalent copper-catalyzed three-component cyclization reaction.The reaction takes thioamides,arylalkynes and alcohols as substrates,tris(triphenylphosphine)cuprous bromide as a catalyst,and trimethylacetic acid as an additive,and is completed at 60°C.In this reaction,alcohol serves both as a nucleophile and as a solvent.The reaction has simple operation,good regioselectivity,and mild reaction conditions,which provides a new route for the synthesis of functionalized thiazole compounds.