Study On The Synthesis Of Pyridyl Conjugated Molecules Oriented By Hypervalent Iodine Salts

Pyridyl conjugated molecules have been widely applied in the field oforganic synthesis, medicine, pesticide, materials, which have the significant value forscientific research and application. However, most of its traditional synthetic methodsare very complex with the require of severe conditions, complex steps, expensivecatalysts, and always contaminate the environment. Hence, it is very crucial to developa novel method for pyridyl conjugated molecules synthesis.In recent years, organic hypervalent iodine reagent has attracted tremendousattention which has emerged multitudinous novel and unique reactivities. What’s more,with the advantages of friendly to environment, convenience for preparation, highselectivity, it has widely used in modern organic synthesis chemistry. At the same time,various structures of organic hypervalent iodine compounds, various novel reactiontypes and its applications have also emerged in these years, which expended itsapplication from traditional acohol oxidation to the synthsis of some compounds withcomplicated structure. As a new kind of organinc synthetic substrate, not only cansynthesis various compounds with different structures rapidly and directly, organichypervalent iodine compounds also have an irreplaceable role on the synthesis ofheterocyclic ring compounds, especially nitrogen ring compounds.Based on our group previous research on hypervalent iodine compounds andthe excellent reactive performance of both2-aminoacetophenone derivatives and pyridyl nitrogen oxides derivatives, we have established a method to synthsispyridyl-conjugated molecules orientedly. The method has an important significance forthe development of organic hypervalent iodine chemistry as well as building nitrogenring compounds with the value of scientific research and appilication, which has thecharacteristic of start meterials available, simple operation, high yield as well as themultiply and orentedly syhthesis for target compound.In this thesis, we synthesized a series of acridine derivatives and2-(9H-pyrido[3,4-b]indol-2-ium-2-yl)phenolate derivatives successfully andeffectively via the reactions that diaryliodonium salts reacted respectively with2-aminoacetophenone derivatives and9H-pyrido[3,4-b]indole2-oxide derivatives. Thereaction conditions including catalyst, solvent, temperature and time were examined.The method is very mild, convenient, effective and little-pollution, which wereunreported previously.Through the two reactions, various kinds of organic reactions were usedsynthetically, such as copper-catalyzed, arylation, aromatization, radical rearrangementand combination.The structures of all the target compounds were confirmed by1H NMR,13CNMR, and HRMS or ESI. In addition, the intermediate was obtained and its structureconfirmed via NMR analysis. The plausible mechanism was also presented.