Tandem Synthesis Of Pyrroloisoquinolines Through 5-Endo Iodolactamization,Oxidative Functionalization And ?-amidoalkylation Reaction

Pyrroloisoquinolines and relative derivatives exhibit considerable pharmacological activities, especially in the area of antidepression and antitumor.Besides, these compounds could be used as important intermediates of some natural products, they have been used widely for the synthesis of alkaloid natural products. In this thesis, the 5-hydroxylpyrrol-2(5H)-ones used as intermediates of Pyrroloisoquinolines also have widely biological activities. Therefore, It is necessary to synthesize some pyrrolidinones and pyrroloisoquinolines.According to reviewing relevant literature, we found pyrroloisoquinolines could be generated from N-phenylpyrrolidinones, which were obtained successfully in our new method. In this thesis, we used ?-iodo-unsaturated phenylacetamide as starting material to react with N-Iodosuccinimide(NIS) and TFA. Finally, a series of1-iodo-10b-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3(10bH)-ones was synthesized through tandem 5-endo iodolactamization, oxidative functionalization and ?-amidoalkylation reaction.In our thesis, we synthesized a series of 1-iodo-10b-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3(10bH)-ones, which were the core structure of erythrina alkaloid group of natural products. At last, the structures of pyrroloisoquinolines have been confirmed by 1H-NMR, 13C-NMR, IR, HRMS and X-ray crystallography of correspounding structure. In addition, we did some studies about the application of target molecular. Possible pathway and mechanism were also explored.