Radical Cascade Cyclization Reactions Of Sulfonylhydrazides And Aliphatic Aldehydes

This thesis mainly aims at the study the radical cascade cyclization reactions of sulfonylhydrazides and aliphatic aldehydes,which chiefly includes the following six chapters: Chapter OneIn the first chapter,we summarized the development of radical sulfonylation reaction from the perspective of various radical sulfonylative precursors.The sulfonyl hydrazide,sodium sulfinate,sulfonyl chloride,sulfinic acid,sulfur dioxide surrogate of DABSO or other sulfonylation reagents have been used as sulfonyl sources for the synthesis of sulfonyl-containing products.Chapter TwoIn the second chapter,A copper-catalyzed oxidative cyclization procedure has been developed for the production of 2-sulfonated 9H-pyrrolo[1,2-?]indol-9-ones via the direct sulfonylation of N-propargyl-substituted indoles with sulfonylhydrazides and tert-butyl hydroperoxide(TBHP).This novel protocol,which tolerates a broad range of functional groups,offers a simple,efficient,and atom-economical route to a series of fluorazones in good yields under mild conditions.Chapter ThreeIn the third chapter,we introduced the radical aryl migration reactions in detail.Radical-initiated aryl migration reactions are of tremendous interest to the radical chemistry and organic synthesis owe to their potential application in chemical community.The combinations of radical reactions with these migrations have been developed to enable the construction of various molecular skeletons that are not easily available through other protocols.We described the recent progress of radical-initiated 1,2-aryl migration and long-distance 1,n-aryl migration.Chapter FourIn the fourth chapter,A novel copper-catalyzed cascade radical sulfonylation of N-propargyl-substituted indoles with concomitant 1,2-aryl migration was described.The protocol provides practical and versatile method of accessing a new class of fascinating 2-sulfonated pyrrolo[1,2-?]indole derivatives in moderate to good yields through the formation of the new C-S,C-C and C=O bonds in a one-step.Chapter FiveIn the fifth chapter,the recent achievements in synthesis of acylative and arylative/alkylative compounds by aldehydes are discussed.Moreover,various types of radical reactions of the aldehydes are described,with their scope of substrates and reaction mechanism.Chapter SixIn the sixth chapter,An efficient metal-free sequential decarbonylative alkylation of N?arylacrylamides with aliphatic aldehydes to provide alkylated phenanthridine derivatives is developed.The reaction undergoes cascade decarbonylation,radical addition,cyano insertion and cyclization processes with aliphatic aldehydes as inexpensive and abundant alkyl radical source,in which one C-N bond and two C-C bonds were formed in one step.