Sythesis Of Novel Chiral Quinoline-Oxazoline Ligands And Their Applications In Iodoamination Cyclization Reaction

The aminohalogenation of alkene is a direct method for obtaining the compounds containing both halogen and amino functional groups. Especially vicinal amines have drawn a substantial attention due to it’s promising application as chemotherapy agents on antitumor therapy. And the halogen atom in the aminohalogenation product has a high reactivity, which can be replaced by other functional groups to generate many other drug intermediates and participate in a variety of other types of reactions. Therefore, the aminohalogenation reaction of alkene has a high research value. This reaction has a long history, however, the aminohalogenation cyclization reaction has emerged as one of the hot topics in recent years.The main content of this paper is divided into four parts. The first chapter summarized the chiral oxazoline ligands in catalysis applications and the recent research on metal-catalyzed aminohalogenation cyclization.The second chapter is the synthesis of novel chiral quinoline oxazoline ligand. 18 kinds of chiral quinoline oxazolines were synthesized in our design, of which 14 kinds were new compounds. And the structures were confirmed by IR, 1H NMR, 13C NMR and HRMS.The third chapter is the copper-catalyzed iodoamination cyclization reaction. Copper-catalyzed iodoamination cyclization of a nitrogen-containing molecules within the terminal olefin was preliminary explored. There are 5 kinds of iodoamination substrates were obtained through the previous method and characterized by IR and 1H NMR. The reaction conditions were optimized. Under the optimised conditions,94% yield was obtained. All the structures of products were confirmed by IR and 1H NMR.All experimental procedures relate to the synthesis was described in detail in the last chapter, and the products date was listed at the same time.