Visible Light-induced Synthesis Of Nitro-containing Heterocyclic Compounds

Nitrogen-containing heterocyclic compounds are an important class of compounds.Among them,3,3-disubstituted indole-2-ones and quinoline-2,4-diones,widely found in natural products and pharmaceuticals have attracted great attention from synthetic chemists.Therefore,it is of great significance to study on the synthesis methodology of nitrogen-containing heterocyclic compounds and the construction of nitrogen-containing heterocyclic compounds library efficiently.Visible light,a clean and renewable resource,can induce the formation of chemical bonds under mild conditions.Visible light-induced oxidative radical addition/cyclization cascade reaction of N-arylacrylamides to afford 3,3-disubstituted indole-2-ones and quinoline-2,4-diones is an economical and efficient synthesis strategy.A variety of functional groups,such as fluoro-containing group,methyl,nitro,and sulfonyl group,have been successfully incorporated into 3,3-disubstituted indole-2-ones and quinoline-2,4-dione skeletons via using different radical precursors.This thesis focuses on the synthesis of difluoromethylated and methylated 3,3-disubstituted indole-2-ones and quinoline-2,4-diones via visible light-induced cascade radical addition/cyclization of N-arylacrylamides under mild conditions.The method exhibits a wide substrate scope and excellent functional group tolerance.Additionally,preliminary experimental study,including of isotope labeling experiment,fluorescence quenching experiment,and control experiment,has revealed a proposed mechanism.