Study On Photochemistry-enabled Cyclization Reaction Of N-Phenyl Cinnamamide Compounds

Recently,great progress has been made in photochemistry-enabled chemical reactions.Visible light is used as a cheap and relatively mild renewable energy.Therefore,this strategy have a good application prospect for the synthesis of complex molecules.In this thesis,we explored the photochemistry-enabled cyclization reaction of N-phenyl cinnamamide to prepare a variety of functionalized 3,4-dihydroquinoline-2(1H)-ones.This thesis is divided into three parts:Chapter one: Research Progress of Organic Reaction Participated by DMSO as a Reagent.In this chapter,the research progress utilizing DMSO as a reagent in organic reactions was described.DMSO as the source of oxygen,carbon or sulfur in various of organic reactions,and participated in reactions as single or dual synthon.Chapter two: Visible-Light-Promoted methyl Radical Cascade Reaction for Constructing 3-methyl-3,4-Dihydroquinolin-2(1H)-onesIn this chapter,a visible-light-promoted methyl radical addition/cyclization reaction cascade was researched.In this investigation,DMSO forms methyl radical in the presence of hydrogen peroxide and ferrous chloride tetrahydrate.resorting to this strategy,we have prepared a variey of methylated 3-methyl-3,4-dihydroquinoline-2(1H)-ones by the irradiation with visible light.The reaction features are simple,mild and environmentally friendly.Chapter three: Visible-Light-Promoted Reaction for Constructing3-hydroxy-3,4-Dihydroquinolin-2(1H)-onesIn this chapter,the cyclization of N-phenyl cinnamamide with benzenesulfonyl chloride promoted by visible light was studied,and the hydroxylated 3-hydroxy-3,4-dihydroquinoline-2(1H)-ones were successfully accessed.The reaction conditions are mild,but its mechanism needs to be further studied.