Simple Synthesis Of Bicyclic Pyridones Heterocyclic Compound

The bicyclic pyridone compound its prominent biological activity to become one of the hotspots of today’s chemical industry, not only has anti-TB, anti-fungal, anti-malarial, anti-diabetic, anti-tumor, anti-inflammatory and other biologically active bicyclic pyridone isdrug and dye common structural unit. Natural purine bases, alkaloids and many important active natural products and organic synthesis intermediates having such a skeleton. The main contents are as follows:1. The benzoyl substituted mercaptals2were synthesized by acetophenone derivatives1. Compound2reacted with ethane-1,2-diamine, propane-1,3-diamine or butane-1,4-diamine to obtain the heterocyclic ketene aminals4a-4p.2. In this thesis, using cheap and easily attained m-nitro iodobenzene or p-nitro iodobenzene5and ethyl propiolate6the key intermediated. The ethyl propiolate6were reacted with m-nitro iodobenzene or p-nitro iodobenzene5under THF as solvent, Et3N and Pd(PPh.3)2Cl2as the catalyst to get substituted nitrobenzene propiolate7a-7b.3. In this disert, heterocyclic ketene amines4and substituted nitrobenzene propiolate7were used as starting materials.twenty-three novel target compounds bicyclic pyridones8a-8w were synthesized under CH3CN as solvent condition with good yields. This synthetic method has the advantages of very simple and efficient.4. All the structures of the target compounds were characterized by1H NMR,13C NMR, IR and HRMS, The structure of8a was characterized by X-ray. The target compounds had not been reported in literatures.5. The synthesis and applications of bicyclic pyridones were also reviewed in this thesis.