Study On Oxidative Dehydrogenative Reactions Of Glycine Derivatives

This thesis is divided into two parts: the first part summarizes the research progress of oxidative dehydrogenative reaction of glycine derivatives. The following contents are reviewed:?1? direct oxidative dehydrogenative coupling of glycine derivatives with nucleophiles to prepare complex ?-amino acid derivatives;?2? oxidative dehydrogenative [4+2] cyclization of glycine derivatives with electron-rich multiple bonds to form substituted quinoline motifs;?3? oxidative dehydrogenative [3+2] cyclization of glycine derivatives with nucleophiles to form heterocycle skeletons;?4? other oxidative dehydrogenative reactions. The second part describes three new developed oxidative dehydrogenative transformations of glycine derivatives.1. Unprecedented auto-oxidative coupling reaction between glycine derivatives and indoles, as well as the auto-oxidative Povarov/aromatization tandem reaction of glycine derivatives with olefins are described. The reactions were performed in the absence of redox-active catalysts and chemical oxidants under mild reaction conditions. Only simple organic solvents and air?or O2? were required.2. Dual catalyst system?C uCl₂-H₂SO₄? promoted aerobic oxidative reaction of glycine derivatives with 2, 3-dihydrofurans or 2, 3-dihydropyrroles were explored, affording an efficient synthesis of high value quinoline fused lactones and lactams. The application of this new methodology to the synthesis of bioactive C ring extension analog of luotonin A has been accomplished in a concise three-step sequence.3. A novel and efficient copper-catalyzed aerobic oxidative dehydrogenative formal [2+3] cyclization of glycine derivatives with ?-angelicalactone is described. A series of complex pyrrolidones were produced under mild and simple reaction conditions. During this research, a green and efficient three-component reaction of easily available anilines, ?-oxoaldehydes and ?-angelicalactone was also developed for the synthesis of highly functionalized pyrrolidones using dilute sulfuric ac id as the catalyst. Products were obtained in good to high yields at room temperature and under solvent- free conditions. The reaction could also be performed on a multi- gram scale with the same efficiency.