Novel Methods For Construction Of C-S /C-O Bond And Its Application In Drug Synthesis

The compounds containing sulfone-group fragment and their derivatives are widely present among various types of pharmaceutical compounds and pesticides, photochemical materials, electronic materials and natural products. Aryl sulfones and sulfonates are very important compounds in which, having a variety of pharmacological and biological activities. Aryl sulfones scaffolds are incorporated in some commercially available drugs such as Bicalutamide(Casodex)(for the treatment of prostate cancer), zolimidine(used for thetreatment of peptic ulcer), Eletriptan(antimigraine medicine). Until now a large number of deficiencies still existing in the synthesis method of these structures. Therefore, the research and improvement of synthtic methods for related structures, in the synthesis of organic compounds and drug s are extremely important.D-glucosamine is reported for the first time as a green ligand for copper catalyzed coupling of aryl halides and sodiumsulfinates, which provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones. When optimal conditions in hand, 12 aryl sulfone compounds has been synthesized and substrate suitability of the catalytic system was extremely broad.An efficient and novel synthtic route to sulfonates derivatives fromm quinoline amide and sulfonic acids was developed in this thesis. In which iodine(III)-Mediated C-H actiation to formation C-O bond. When optimal conditions in hand we expanded substrate and obtained 20 sulfonates containing quinoline amide in very high isolated yields, at last.we confirmed structure of the reaction product further by X- crystal diffraction.In this thesis, 45 compouds were synthesized and these compounds were fully characterized by 1H-NMR、13C-NMR、GC-MS and IR.