N-bromosuccinimide Promoted The Transformation Of The Sulfonamide

N-bromosuccinimide(NBS)is a useful brominating agent.It traditionally was used in allylic hydrogen,benzylic hydrogen,and a-position hydrogen of carbonyl bromo.Meanwhile,NBS can also be used as the catalyst,the oxidizing agent and the polymerization reaction initiator and so on.NBS has a high degree of selectivity and low-cost advantages,so expanding the value of NBS in organic synthesis is of great significance.This thesis researched the NBS promoting the synthesis of sulfonylimide and N,N'-sulfonamide amine compound.Main contents are as follows:On the basis of literatures,The applications of the NBS in organic synthesis were reviewed;the synthesis of imide and N,N'-sulfonamide compounds were introduced.The second chapter,Under the action of NBS reagent and a base,with p-toluene sulfonic acid amide as a raw material,we synthesized nine different toluene sulfonic acid imide compounds,and the isolated yields were 46-63%.The synthetic method was based on NBS as the oxidant,The synthetic method had mild reaction conditions and good selectivity advantages.Meanwhile,we optimized kinds of solvents,different kinds of bases,the amount of base and the ratio of materials.Through the optimization of the reaction conditions,We obtained the optimum process parameters as follows:1,4-dioxane as the reaction solvent,NBS as Bromo-agent,and the amount of 120%,DACBO as the base,and the amount of 100%,under the room temperature,reaction for 3h.The third chapter,with alkyl amines and substituted anilines synthesis of the corresponding substrate,then with these substrates,Under the action of NBS and a base,we successfully synthesized 18 different N,N'-p-toluene sulfonyl amine compounds,and the isolated yields were 53-79%.The synthetic method had mild reaction conditions,easy operation and cheap raw materials advantages.Meanwhile,we optimized kinds of solvents,different kinds of bases,the amount of base and the ratio of materials.Through the optimization of the reaction conditions,We obtained the optimum process parameters as follows:CH2Cl2 as the reaction solvent,NBS as initiator,and the amount of 160%,K2CO3 as the base,and the amount of 60%,under the room temperature,reaction for 3h.This thesis has expanded the scope of application of the NBS reagent,and it has theoretical significance and innovation.