Synthesis Of Bicyclic Pyridone/1,3-oxazine And Isoquinolinone Compounds

The bicyclic pyridone compounds have good biological activity,and the parent structure units of many of the listed drugs are the structure of the bicyclic pyridone Therefore,it is of great significance for the study of bicyclic pyridone.As one of the most important structural units,1,3-oxazinane has been paid more and more attention.up to now,there are very few reports about this kind of compounds in the literature,and these compounds have been reported to have pharmacological activities such as antibacterial and anti-reverse transcriptase inhibitors.Therefore,it is more and more important to explore new synthetic routes to synthesize 1.3-derivatives.Based on the importance of bicyclic pyridone and 1,3-oxazinane,the activity of isoquinolone compounds,the main work of this paper is focused on the following aspects:The first chapter:The properties of heterocyclic ketene aminals,bicyclic pyridone compounds,1,3-oxazinane compounds,isoquinoline imine derivatives and isoquinolone derivatives were briefly reviewed.The second chapter:There are 16 bicyclic pyridone compounds have been synthesised via the regioselective condensation reaction of heterocyclic ketene aminals(HKAs)with ethyl 2-cyano-3,3-bis(methylthio)-acrylate in xylene at refluxing temperature,the yield was 68%-92%.On the other hand,in xylene solvent,five membered heterocycle ketene aminals and ethyl 2-cyano-3,3-bis(methylthio)acrylate or 2-(bis(methylthio)methylene)malononitril,heating reflux using cesium carbonate as alkaaline conditions,synthesized 20 1,3-oxazinane compounds.The yield is up to 76%?87%.The third chapter:The establishment of xylene as solvent,refluxing conditions,we reacted 3,3-bis(methylthio)-1-phenylprop-2-en-1-one with the compounds phenylmethanamine or 2-phenylethan-l-amine,one-step formation of 1,1-ene diamine compounds,29 compounds were synthesized,the yield was 66%?90%.Follwed by the 1,1-ene diamine compounds and 2,4,5,6-tetrafluoroisophthalonitrile reacted at normal temperature,with 1,4-dioxane and acetone as solvent,simple and convenient synthesis of 30 isoquinolone compounds,the yield was 74%?89%.Bicyclic pyridone compounds,1,3-oxazinane compounds and isoquinolone compounds were characterized 1HNMR,13CNMR,IR,HRMS,all these compounds were verified by X-ray diffraction.