Study On Difunctionalization Of Unsaturated Amides For The Synthesis Of Oxindoles

The Oxindoles widely exist in various natural products with biological and physiological activity, drug molecules, pesticides and functional materials. Clinical medicine shows that oxindoles can inhibit enzymes and achieve good results in the treatment of tumors. Therefore, the development of a novel, efficient and environment benign method for the synthesis of oxindoles attract more and more interest.There are three parts in the dissertion, which mainly describes several effective methods of the synthesis of small molecule drugs of oxindoles, in order to find a more efficient and simple method for synthesis of oxindoles with potential physiological activity.The first chapter of this dissertion reports the reseach progress on the previous methods for the synthesis of oxindoles, and introduces its important application value in the modern organic synthesis.The second chapter of this dissertion mainly describes a new method for the synthesis of oxindoles, which is the cycloaddtion of N-methyl-N-phenylmethacrylamide with solvent under the visible-light as catalysis. The expriements show: in the presence of Ru(bpy)3Cl2 as catalyst, Na2CO3 as base, 4-MeOC6H4N2BF4 as initiator, N-methyl-N-phenylmethacryl-amide and acetonitrile or acetone as reaction substrates under the 36 W compact florescent light, and stirring under the reaction temperature of 50 oC, the reaction spend 20 hours can get oxindoles with a good yield.The third chapter is mainly to study methods for the synthesis of the stereoselective production of(E)-3-arylylideneoxindoles. In the presence of Pd(OAc)2 and Na2CO3, a vaitety of N-arylpropiolamides underwent the C-H activation reaction with aryl diazonium salts to selectively afford the corresponding oxindoles in moderate yield.