Study On The Reaction Of Diaryliodonium Salts In Synthesis Of Bis(thioaryl)imines Compounds

The imine compounds(-C=N-),which shows a wide range of biological activities,is one of the most important and commonly used intermediates in organic synthesis.Among them,thioimines(RS-C=N-)are representative compounds.In addition to the general reactions of C=N bond,such as reduction,cyclization and nucleophilic addition,the C-S bonds of thioimines also exhibit ordinary chemical reactions,such as insertion or transition metal catalyzed cross-coupling reaction.In the first chapter,the recent reactions involving diaryliodonium salts and isothiocyanates have been summarized.Hypervalent iodine compounds have been received widely attentions in modern organic synthesis as mild,easily avaliable,highly selective and environmentally friendly reagents.Isothiocyanate(R-N=C=S)is well known to be easily prepared,good stability,commonly used as organic synthesis intermediate,and widely used in the synthesis of heterocyclic compounds.In the second chapter,a new copper-catalyzed reaction for the synthesis of bis(arylthio)imides was established using isothiocyanates and diaryliodonium salts.The reaction process has been involved arylation,nucleophilic addition,C-S clesvage and C-S bond formation process,which showed mild reaction conditions and broad functional group tolerance.Functionalized bis(arylthio)imines were potential imine structural units with two arylthio groups that could be used for further conversion into more valuable compounds.In the third chapter,a highly efficient synthesis method of 2-thioquinoline derivatives was carried out by the reaction of isothiocyanate with diaryliodonium salt under copper-catalyzed.2-Thioquinoline has potential hallucinogenic activity,special antibacterial and so on.At present,the method to synthesize 2-(phenylthio)quinoline is using 2-haloquinoline and benzenethiol.Therefore,it is of great significance to develop a new synthetic method which is environmentally friendly and efficient.