Synthesis Of Cbz-nsulfilimine And Preparation Of Its Derivative Cbz-Nsulfoximine

Sulfilimides and their derivatives sulfoxidimides are very important intermediates compounds,which have special biological activities.Especially in the medical field,pesticide field and biological field which have very important research value,such as:anti-cancer,anti-inflammatory,anti-virus and so on.Therefore,these sulfoxide compounds are widely restricted.However,synthesis of such sulfonamides involves the formation of S-N and S-O bonds,which reactions are related to organic solvents.Therefore,a way for green and economical synthesis method is not only an important research of organic synthesis methodology,but also it is of great significance to the development of medical and pharmaceutical fields.Based on the above reasons,the research work of this paper mainly includes two parts:1 Sulfilimines were synthesized by the combination of Cbz-N amination reagent with thioether:water was used as solvent,calcium oxide as base,methyl phenyl thioether and Cbz-N compound were used as substrates to react in the?oposition of the Cbz-N compoundto produce sulilimines.First,we investigate and optimize the reaction conditions to obtain the best reaction conditions.Then,under the best reaction conditions,the applicable range of substrates was investigated and the products were analyzed by NMR.Finally,we explored the reaction mechanism of synthesis of Cbz-N sulfilimines and proposed a reasonable reaction mechanism.The synthesis method has the following advantages:no catalyst,suitable reaction conditions,simple reprocessing,wide range of reactants,and good yield.This work provides an effective method for the synthesis of imines.2 Cbz-Nsulfoximide compounds were constructed by oxidation of Cbz-Nsulfilimines:KMnO₄ in water and 3-Chloroperbenzoic?m-CPBA?acidin ethanol had good oxidation property,and the Cbz-Nsulfilimine compounds were oxidized to Cbz-Nsulfoximide compounds.Among them,m-CPBA as the oxidation product of oxidant sulfoximide is up to 90%.Compared with the traditional method,this method has the advantages of simplicity and efficiency.A series of Cbz-Nsulfoximide compounds were synthesized by this method.And the products were analyzed by ¹H NMR and ¹³C NMR.