The Reaction Of Sulfonyl Chloride And Imine

β-lactam is the important unit ofβ-lactam antibiotics.β-sultam is the sulfur analogue ofβ-lactam, so the exploration of the reaction of sulfonyl chlorides and cyclic imines to yield polycyclic compounds containingβ-sultam is significant for discovering new drugs.In this dissertation, the differences of the two oxidated methods by NCS and chlorine to synthesize sulfonyl chlorides have been first discussed. Then as the mild conditions it required and simple operation of NCS oxidation, NCS has been chosen to synthesize a series of different substituted-sulfonyl chlorides starting from thiols, thioesters and disulfides. In addition, a variety of cyclic imines have been synthesized through different methods according to corresponding literatures. Moreover, the requirements of the starting materials and reaction conditions have been determined by the reaction of benzyl sulfonyl chloride and chain imine. The results showed that corresponding cis-and trans-β-sultams were generated in the reaction of benzyl sulfonyl chloride with benzylidene benzylamine, but no product when reacting with benzylidene aniline, which indicated that this reaction only occurred to N-alkyl substituted imines. In addition, the reaction of benzyl sulfonyl chloride and benzylidene benzylamine could not produceβ-sultam but 1,2-diphenyl ethylene when triethylamine was added to the system, which indicated that the expected reaction occurred only with the excess imine as base but not with triethylamine.Then the reactions of several sulfonyl chlorides with different cyclic imines have been studied. The expected bicyclicβ-sultams were not generated, instead a series of new compounds were obtained, the structures of which were confirmed by various characterization means.