Photoinduced Electron Donor-acceptor Complex Promotes The Synthesis Of Oxyindole And Isoindolone

In recent years,photochemistry has developed into an important method for the construction of compounds in synthetic chemistry and medicinal chemistry.However,traditional photoreactions usually require the addition of expensive metal complexes and hard-to-degrade organic dyes as photocatalysts.In recent years,organic photoreactions promoted by electron donor-acceptor(EDA)complexes have been widely developed.The complexes can generate free radicals under mild conditions and realize the coupling reaction of radicals.This strategy has become an important organic synthesis method.But it still faces certain limitations,such as the formation of electron donor-acceptor(EDA)complex often requires specific compounds,and the mechanism of action is not clear.Indole oxide compounds have antiviral,antifungal,antibacterial,antiproliferative,anticancer,anti-inflammatory,antihypertensive and anticonvulsant biological activities,it is widely used in pesticides,medicine,dyes,feed,food and additives and other fields,and its new application fields are constantly being developed.Therefore,this thesis a series of potential biological activity oxyindole and isoindolone compounds are constructed by electron donor-acceptor(EDA)complex with clear modes of action.The thesis including the following two work: The first part of the work is photoinduced halogen-bonding enabled synthesis of oxindoles and isoindolinones from aryl iodides.In the reaction,DBU can serve as a suitable halogen-bonding acceptor with aryl halides for the formation of a photoactive electron donor and acceptor complex.The complex generation of aryl radicals from aryl halides under blue light irradiation and applied it in radical generation/1,5-hydrogen-atom transfer/radical cyclization cascade reactions for the synthesis of oxindoles and isoindolinones.The second part of the work is electron donor-acceptor complex enabled cascade reaction of unprotected o-anilide aryl chlorides for heterocycle synthesis.A novel electron donor-acceptor(EDA)complex strategy is developed to promote the coupling reaction of aryl chloride.It enables the activation of low-activity aryl chloride compounds in the absence of photocatalysts.And it constructs a series of oxidized indole compounds.We then will explore the effect of oxyindole compounds of different structures on their biological activity.