Chemoselective Arylation Study Of Isatin-3-Oxime And 2-Aminopyridine

This thesis mainly consists of three parts: review of the development and applications of arynes,the studies of selective N-arylation reactions of arynes with isatin-3-oxime and 2-aminopyridine derivatives Chapter 1: Review of electrophilic addition reactions of arynesIn this chapter,the background of arynes was introduced,including discovery and improvement of the preparation methods,and the electrophilic addition reactions of arynes also were reviewed.Chapter 2: Studies on chemoselective N-arylation reaction of isatin-3-oxime with arynesIn this chapter,the reactions of the chemoselective N-arylation of isatin-3-oxime with arynes were explored.Nitrones are not only widely recognized as important building blocks in the synthesis of various natural and biologically active compounds,but also used as both spin-trap reagents and therapeutic agents.Although many approaches to prepare isatin ketonitrones have been developed,these strategies often suffer from some drawbacks.Therefore,we intend to prepare nitrone compounds using arynes with isatin-3-oxime derivatives.However,the experimental results showed that the O-arylation products were obtained as the sole product.Chapter 3: Studies on chemoselective N-arylation reaction of 2-aminopyridine derivatives with arynes.In this chapter,1-arylpyridin-2(1H)-imine motif was widely found in bioactive molecules and therapeutic agents.However,synthetic approaches to access this unique and simple unit have been rarely developed.Considering the importance of this motif(i.e.,1-arylpyridin-2(1H)-imine)and the lack of efficient strategy for its synthesis,we developed a facile protocol utilizing N-arylation reaction of 2-aminopyridines with arynes.