Studies On Radical Cyclization Of N-benzenesulfonic/ben Zoyl Acrylamides

Nitrogen-containing heterocycle indolones and isoquinolinediones server as important structural units of pharmaceutical compounds,and effective synthesis of them will be of great theoretical and practical significance.In recent years,the development of"green","efficient"and"economic"synthesis methods for quinolines and indole ketones are currently one of the hotspots in the field of organic synthesis and medicinal chemistry.Basing on the literatures and the our previous work,this dissertation focus on the development of synthetic methodology for the oxindoles and isoquinolinodiones.The main contents are as follows:First,the current research progress on free radical mediated tandem radical addition/cyclization of alkenes for the synthesis of oxindoles and isoquinolinodiones was reviewed.In the second part,the visible-light-induced desulfone/cyclization of tosyl amides for the synthesis of oxindoles orα-aryl-fluoroalkyl amide was developed.Using perfluorinated alkyl iodides or bromides as the fluoride source,N-butyl-N-（tolylsulfonyl）methylacrylamides underwent tandem radical addition/β-arylmigration/desulfonylation by fac-Ir（ppy）₃ under LED irradiation,leading to a series of perfluoroalkylating oxindoles andα-aryl-fluoroalkyl amides.It provides a efficient and quick entry for the preparation of fluorinated oxindolesand alpha-aromatic amide with potential biological activities.The process features wide substrate scope,mild reaction conditions（room temperature）,green catalytic system.The last part,a method for the synthesis of isoquinolinediones was developed.The alkyl azo reagents reacted with 3-halogenated benzamide suffering tandem radical cyclization.With the alkyl azo reagents（AIBN）as free radicals source,the 3-halogenated benzamide underwent radical cyclization,leading to a series of isoquinoline-1,3（2H,4H）-diones with site-selectivity.The protocol features easy-prepared substrates and cheap catalytic systems...