Synthesis Of 2-Aroylindoles Via Palladium Catalyzed Intramolecular C-N Coupling Reaction And [3+2] Cycloaddition Of Aziridines

The thesis was consisted of two parts.Part one was synthesis of2-aroylindole compounds via Palladium catalyzed intramolecular C-N coupling reaction.The second part focused on the [3+2] cycloaddition of aziridines and ethyl acrylate.Part one was consisted of three chapters.The first chapter reviewed the biological activities and the common synthesis of 2-aroylindoles.The second chapter focused on the Palladium catalyzed intramolecular C-N coupling in synthesis of many important heterocyclic compounds,such as carbazoles,lactams,indazoles,indolines and indole derivatives.These reactions were with moderate to good yields and good tolerance.The third chapter proposed the intramolecular C-N coupling cyclization of(Z)-4-methyl-N-(3-oxo-1,3-diphenylprop-1-en-2-yl)benzenesulfonamides catalyzed by Palladium catalysts.The cyclization products were2-aroylindoles.This was the first report on the synthesis of 2-aroylindolesthrough Palladium-catalyzed C-N coupling reaction employingα,β-dehydroamino derivatives as substrates.In order to obtain more satisfactory results,a series of experiments were carried out using different conditions.With the optimized reaction conditions in hand,various substituted(Z)-4-methyl-N-(3-oxo-1,3-diphenylprop-1-en-2-yl)benzenesulfonamides were used to test the generality of the reaction.Eleven 2-aroylindoles were synthesized with 41-82% yields.This method took the advantages of high atom-economy for Oxygen as the terminal oxidant.The second part described [3+2]-cycloaddition of aziridines and unsaturated bonds for the synthesis of heterocyclic compounds.Phenyl(3-phenylaziridin-2-yl)methanone and ethyl acrylate were applied in the direct synthesis of polysubstituted pyrroles via [3+2] cycloaddition.We also discussed the influencing factors,such as catalysts,solvents,temperature and additives.This method provided a new idea for synthesis of multisubstituted pyrroles without any metal catalysts.The reaction also needed further reaserch for moderate yields and regioselectivity.