Applications Of The C-H Functionalization Reaction And The Cycloaddition Reaction In The Synthesis Of Cyclic Compounds

As the basic framework of natural products and pharmaceutical, cyclic compounds, especially heterocyclic compounds showed good drug activity, biological activity, high ceiling and so on. However, the synthesis of cyclic compounds often exist many problems, such as a single bond mode, which requires a lot of steps, the polycyclic compound, which is difficult to construct and so on, Therefore, it is still one of the most challenging tasks in organic synthesis to find new compounds.This dissertation mainly studies on the applications of the C-H functionalization reaction and the cycloaddition reaction in the synthesis of cyclic compounds. And we’ve achieved a series of meaningful experimental results.1. In argon atmosphere and the presence of CoCl2, DTBP and K2HPO4, an efficient type of oxidative difunctionalization of N-aryl-N-(arylsulfonyl)alkenes with the oxidative deprotonation of cyclohexane on sp3 C-H has been studied and proceeds by 1,4-aryl migration incorporation. We have synthesized sexenteen cyclic compounds, and fromed 2’,3’-dihydrospiro[cycloheptane-1,1’-indene]. All of them were characterized by 1H NMR,13C NMR, GC-MS, HRMS spectroscopy. The single crystal structures of two products were determined by X-ray diffraction method.2. In argon atmosphere and the presence of TBPB and K2HPO4, an efficient type of oxidative difunctionalization of N-aryl-N-(arylsulfonyl)alkenes with the oxidative deprotonation of tetrahydrofuran on sp3 C-H has been studied and proceeds by 1,4-aryl migration incorporation. We have synthesized nine cyclic compounds, and fromed 2’,3’,4,5-tetrahydro-3H-spiro[furan-2, 1’-indene]. All of them were characterized by 1H NMR,13C NMR, GCMS, HRMS spectroscopy.3. This chapter focuses on the synthesis of 2,5-dihydrofuran-3-carboxylate by using the cycloaddition reaction. We have synthesized 14 cyclic compounds, and all of them were characterized by 1H NMR,13C NMR, IR, HRMS spectroscopy. The single crystal structures of two products were determined by X-ray diffraction method.