Studies On The Synthesis And Properties Of Some Compounds Including Nitrogen Atoms

Organic compound including nitrogen atoms is a privileged core structural motif found in the field of organic synthesis and medicine. From the point of view of pharmaceutical chemistry, there are two kinds of structures are very attractive and are also very challenging:all substituted heterocyclic and chiral heterocyclic. This paper is focused on the studies on the synthesis and properties of some compounds including nitrogen atoms and has three parts.Firstly, we have developed the strategy of neighboring lithium-assisted [1,2]-Wittig rearrangement (NLAWR strategy), it can apply not only to chiral Ar-BINMOLS ligands, but also to Betti base-derived benzyl ethers to construct γ-amino alcohols. The corresponding products were obtained in promising isolated yields (up to 79%). It is interesting to find that the highly diastereoselective [1,2]-Wittig rearrangement of Betti base-derived benzyl ethers gave the corresponding chiral amino alcohols in highly diastereoselective manner (>99.9% de). The complete chirality transfer provides an unprecedented strategy for the stereoselective construction of substituted amino alcohols from simple primary amine. More importantly, we have demonstrated that the optically pure amino alcohols could be converted into all substituted pyrrolidine derivatives bearing multiple stereogenic centers through intramolecular cyclization.Then, we have described an intersting finding that the one-pot three-component click reaction could be performed smoothly under mild conditions to give various 1,2, 3-triazoles in moderate to good yields with the mediation of secondary amine functional polysiloxane. At the same time, we have discovered firstly that a new type of fluorescent sensor with cyclic or acyclic BINOL skeleton containing triazole groups, showed high fluorescence emission and high selective recognition for iodide.Finally, we have developed the first nickel-catalyzed C2-thiolation of indolepyrimidyl C-H bonds with disulfides, not by classical chemical method, but by new method of transition-metal-catalyzed C-H bond functionalization.