Study On The Reaction Of 2-Mercaptosyl Compounds With High Iodine Salts

Aryl sulfide compounds are a very important class of organic substances,especially heterocyclic aryl sulfides,which play an important role in the field of drug synthesis and functional materials.Therefore,it is necessary to continuously explore more efficient sulfide synthesis strategies.Because of its easy preparation,low cost,mild reaction conditions and high reactivity,diaryliodonium salts are used as good nucleophiles in organic synthesis.In this paper,linear and cyclic diaryliodonium salts were used as raw materials to react with 2-mercaptoazole compounds,and C-S bonds were formed efficiently and environmentally.This paper is mainly introduced from the following aspects:?1?Various methods for forming C-S bonds are introduced.,including transition metal?Pd,Ni,Cu?catalyzed reaction of aryl halides,aryl boronic acids,aryl trifluoromethanesulfonic acid with mercaptans,and no transition metal-catalyzed reaction of sulfinyl or sulfonyl-benzimidazole,linear diaryliodonium salt,N-toluenesulfonylhydrazide,acetonitrile with mercaptan.There are also reactions in which metal sulfides,organic disulfides are used as sulfur source.?2?In this study,the benzimidazole[2,1-b] thiazole derivatives were synthesized by the reaction of 2-mercaptoimidazole derivatives with diaryliodonium salt containing terminal alkynes at room temperature without the existence of metal catalysts,ligands and alkalis.The target compounds were characterized by ¹H NMR,¹³ C NMR,single crystal X-ray and HRMS,and exploring the best conditions for this experiment.It showed that the yield of target product was 84% when the molar ratio of benzo-2-mercaptobenzimidazole to diaryliodonium salt was 1:1,dichloromethane was used as solvent,and the reaction time was 12 h at room temperature.At the same time,the mechanism of the reaction was discussed,and the effects of different concentrations of these compounds on the growth of human hepatoma cells?Hep G2?were studied by MTT method.The results showed that compound 3b had a strong inhibitory activity against Hep G2 cell proliferation at a concentration of 4 ug·ml-1,and the inhibition rate was 52%.?3?The reaction of cyclic diaryl iodonium salt and 2-mercaptobenzoxazole was investigated,and various benzo-heterocyclic aryl sulfide compounds were synthesized.The targets were analyzed by ¹H NMR,¹³ C NMR and HRMS.And the optimal conditions for this experiment were determined.When the molar ratio of the 2-mercaptobenzoxazole compound to the cyclic diaryliodonium salt is 1:1.2,the solvent is DMF,the base is K₂CO₃,the catalyst is Cu I?10 mmol%?and the reaction time is 12 h at a temperature of 130 ?.the yield can reach 95%.The reaction uses only a small amount of catalyst.At the same time,the use of cyclic diaryliodonium salts increases atomic economy and reduces environmental pollution..