The Study On Reactions Of N-(Phenylsulfonylmethyl)-4-Methylbenzene-Sulfonamide With Organocopper Reagents

A lot of Sulfonamides play an important role in natural products and drugs.The Mannich condensations of p-toluene sulfonamide, aliphatic or aromatic aldehydes with sodium sulfinates afford a series of N-(Phenylsulfonylmethyl)-4-Methyl-benzenesulfonamides.We synthesized thirteen kinds of N-(Phenylsulfonylmethyl)-4-Methylbenzenesulfonamides, five of which are not found in literatures.In many literatures, the N-(Phenylsulfonylmethyl)-4-Methylbenzenesulfonamides always react with nucleophiles after changing into N-sulfonylimines.On this basis, we focus on the reactions of these thirteen kinds of N-(Phenylsulfonylmethyl)-4-Methylbenzene-sulfonamide with organcopper reagents.By the way of changing the proportion of the reactants, time, and the temperature, we obtained seven kinds of compounds, one of which is not found in literatures.Besides, we attempt to study on the reactions of different kinds of N-(Phenylsulfonylmethyl)-4-Methylbenzenesulfonamides with organocopper reagents.And a possible reaction mechanism is proposed about an elimination-addition process.The reaction condition is mild, the materials are cheap and easy to get, and the yield is high. The structures of the expected products are confirmed by IR spectrum, 1H NMR spectrum, and 13C NMR spectrum.The study explored a new way for the synthesis ofp-methylbenzensulfonamido compounds.In addition,4-benzyl-2-oxazolidinone was made from phenylalanine by three steps of reduction; esterification and cyclization.We also studied the synthesis of 4-benzyl-3-(1-phenylsulfonylethyl)-2-oxazolidinone, and intend to study the reaction with organocopper reagents.