Silver Mediated Indole Dearomatization-Synthesis Of Sulfone C3 Spiroindoles

C3 spiroindoles are common and widely used functional organic molecules in natural products and alkaloids.Because of its remarkable biological activity,it has been widely used in different fields such as medical drugs,pesticides and cutting-edge biomaterials,it has become one of the research hotspots of synthetic chemists and pharmaceutical chemists.In 2010,C3 spiroindoles were successfully isolated.Since then,chemists have developed more and more strategies to synthesize C3 spiroindole,and various important functional groups(such as trifluoromethyl,azide,halogen,phosphonyl,sulfonyl,etc.)have been integrated into the framework of C3 位spiroindole,which gives it novel properties.At the same time,new synthetic methods are still being explored and developed.In recent years,three strategies have been used to synthesize C3 spiroindoles: interrupt Fischer indole synthesis,indole dearomatization and condensation.With indole as substrate and with the participation of various transition metals,the functionalized C3 spiroindole compounds developed rapidly through dearomatization/tandem cyclization reaction.In this paper,we focus on the silver promoted dearomatization/sulfonylation tandem cyclization of indole acrylamide,and obtain a series of sulfonylated C3 spiroindoles.After selecting and optimizing the reaction conditions,we determined the optimal reaction conditions,and then investigated the universality of the substrate and the application of the product.At the same time,through verification experiments,the reaction mechanism was elaborated.The most important thing is that the reaction is suitable for gram-scale reaction.This thesis mainly divided into three chapters:In the first chapter,the progress of the synthesis of C3 spiroindoles with transition metals is reviewed.In the second chapter,we obtained a series of sulfonylated C3 spiroindoles by means of silver-promoted dearomatization/sulfonylation tandem cyclization of indole acrylamide.The method also showed the construction and sulfonylation of C3 spironindole.This strategy is easy to obtain raw materials,easy to operate,and the reaction conditions are mild,the substrate is universal.In the last chapter,conclusion and prospect.Based on the existing dearomatization/sulfonylation tandem cyclization reactions of indole acrylamide promoted by silver,we will continue to study the sulfonylation reactions of other indole substrates,in the hope of further synthesizing rich structure of sulfone containing C3 spiroindole compounds.