Oxidative Coupling Reactions Of N-Containing Heterocylic Compounds In The Organic Synthesis

This thesis describes my graduate study which involves applying the oxidative coupling reactions to the synthesis of N-heterocycles Compounds in the organic synthesis. It consists of three chapters.In the first chapter, the recent progress on the hypervalent iodine-catalyzed oxidative reactions in organic synthesis is briefly reviewed. Both the aryl iodides and iodides based catalytic oxiding systems are dealt with in this part.The second and the third chapters are my research work. In the second chapter, a new method for the synthesis of3-acetyloxindoles is desribed. This method employs the intramolecular oxidative coupling of acetoacetanilides which is made possible by using Ag2O as oxidant in the presence of CS2CO3; The third chapter describes our findings that tetrabutyl ammonium iodide is capable of catalyzing the direct oxidative C-N coupling of2-aminopyridines with β-keto esters and1,3-diones, which affords imidazo[1,2-a]pyridines as the products. The reaction was realized under metal-free conditions by using tert-butyl hydroperoxide (TBHP) as oxidant BF3Et2O as cocatalyst. The reaction provides a simple and efficient approach to the synthesis of imidazo[1,2-a]pyridines.