Study On The Copper-Catalyzed Synthesis Of Oxazolidinone And Thiazolidinthione Derivatives

Copper-catalyzed Ullmann-type C-O, C-N, and C-S formation reactions are powerful tools in organic synthesis as well as in heterocyclic compound synthesis. In this thesis, we synthesized three series of nitrogen atom containing heterocyclics totally38compounds from N-(2-bromoallyl)-amines and carbon dioxide or carbon disulfide. The research results are summarized as follow:1. A novel copper-catalyzed cascade reactions synthesis of1,3-oxazolidin-2-ones which were obtained via the reaction of N-(2-bromoallyl)amines and KHCO3.The CO2produced from heated KHCO3reacted with N-(2-bromoallyl)amine to form the carbamic acid salt. The sequential copper-catalyzed intramolecular Ullmann vinylation could offer the corresponding1,3-oxazolidin-2-ones in moderate to good yields. Our procedure has some advantages such as easy operation, environmental friendness, and higher yields.2. New approaches to the synthesis of1,3-thiazolidine-2-thiones and1,3-thiazole-2-thiones have been developed. By controlling the reaction temperature, the above two kinds of heterocyclics were obtained respectively from the copper-catalyzed reaction of N-(2-bromoallyl)-amines with CS2. This "one-pot" synthesis has some advantages such as high efficiency, high selectivity and higher yields, in which N-C and S-C bonds were formed in one sequcence.