Study On Methylthiolation Of Sulfoxide Compounds

As an important intermediate,sulfoxide compounds are widely used in the fields of fine chemicals,organic synthesis,pesticide,medicine,printing and dyeing,synthetic fibers,rare metal extraction agents and plastics.It is important for aryl sulfide to be as natural material,basic medicine and functional materials.Thiomethyl group can improve the optical properties of the compounds.Therefore,developing an effective method to construct the C-S bond has become a hot spot in recent years.With of its high electron-withdrawing effect and admirable lipophilicity(πR = 1.44)which could improve the drug molecule’s cellmembrane permeability and enhance its chemical and metabolic stability,compounds bearing this group are potentially important targets in the pharmaceutical and agrochemical fields.As a starting point,in this paper,the 3-position trifluormethylsulfenyl chloride is used as the methylthio-reagent,the indole and its derivatives and its derivatives are subjected to 3-position methylthio,the optimal reaction conditions for synthesizing 3-methylthio indole were as follows:3 eq of dimethyl sulfoxide,1 eq of anhydrous copper acetate,2 eq of diethyl phosphite,toluene as reaction solvent,reaction temperature 110 ℃ reaction time 18 h,and product yield up to 92%.And the three-fluoromethylsulphinyl chloride is used as the trifluoromethylthio-reagent,and the indole and its derivatives and the olefin compound are subjected to three-position trifluoromethylthio.The optimum reaction conditions for the synthesis of 3-trifluoromethyl thioindole were as follows:2.5 eq of trifluoromethyl sulfonyl chloride,acetonitrile as solvent,reaction temperature 90 ℃.The reaction time was 6 h(the reaction time of bifunctional group product was 18 h)and the yield of the product was up to 90%.The optimum reaction conditions were as follows:2.5 eq of trifluoromethyl sulfonyl chloride,N,N-dimethy;formamide as solvent,reaction temperature 90 ℃ and reaction time 1 h.The yield of the product is up to 90%.Trifluoromethylsulfinyl chloride is used as a trifluoromethylthiolation reagent for the first time,which is simple in operation and high in yield.And 66 kinds of compounds were synthesized.The products were characterized by 1H NMR,13C NMR,19F NMR.