The Study Of Selective Selenization And Difluoroalkylation Of N-heterocyclic Compounds

Indoline and oxazolidinone are typical structural motifs which were widely found in a variety of pharmaceutically relevant drug candidates and natural products.Therefore,the synthesis and modification of these two types of compounds have received considerable attention in recent years.In this thesis,we focus our attention on the research of C₅ C–H selenylation of indoline and the C₄ C–H difluoroalkylation of oxazolidinone.Chapter 1.PIDA-promoted C–H selenylation of indoline compounds on the C₅ position.The reaction has excellent chemical selectivity and position selectivity.Indoline and diaryl diselenide compounds that bearing different substituents could be converted efficiently,delivering a series of asymmetric diaryl selenides in high yield.The bioactive molecules also compatible under this reaction codition,affording the corresponding selenylated products in good yields.Notably,the directing group could be removed easily under mild conditions.Chapter 2.Palladium-catalyzed C₄ difluoroalkylation of oxazolidinones.Typical feathers of this reaction including good functional group tolerance,highly yield as well as the completely para-selectivity,thus provide an economical,convenient and green strategy for the structural modification of oxazolidinones.Furthermore,the introduced difluoroalkyl groups could be further converted into useful alcohol,carboxylic acid,amide derivatives under mild reaction conditions.Among them,carboxylic acid derivatives can be further converted into trifluoromethylated products.