Study On The Radical Coupling Reactions With Cyclopropanols And Diselenides

Quinoline derivatives and organoselenium compounds widely exist in many compounds and natural products with good biological and pharmacological activities.In recent years,the synthesis of quinoline derivatives by ring-opening/cross coupling strategy of cyclopropanols and the synthesis of complex organoselenium compounds by the diselenides have become two of the hotspots in current study.At present,the ring-opening reaction of cyclopropanols and the selenylation reaction of the diselenides are mainly carried out under the catalysis of Cu,Ag,Mn,Co and other metals or under the condition of oxidant with chemical equivalent.Therefore,the development of simple,mild and economical methods for the synthesis of these complex compounds has become the hot field of organic synthesis/drug synthesis.In this thesis,the research progress of cyclopropanol ring-opening reaction,selenylation reaction involving diphenyl diselenides and quinoline ring functionalization were reviewed.The ring-opening reaction of cyclopropanol catalyzed by photocatalyst is realized,and selenylation reaction of o-divinylbenzenes derivatives and functionalization of quinoline derivatives are also realized.This thesis provides mild and efficient methods for the synthesis of β-carbonyl alkyl-substituted quinoline compounds and multi-substituted selenium-containing dihydroisobenzofuran derivatives.The main work of this thesis is as follows:In chapter one,the research status of ring opening coupling reaction of cyclopropanols,selenylation reaction of diphenyl diselenides and functionalization of quinoline derivatives are reviewed.The second chapter introduces the experimental materials,reagents and methods.The third chapter presents the ring opening coupling reaction of cyclopropanols and alkylation reaction of quinoline derivatives,which provides a simple and effective method for the synthesis of β-carbonyl alkyl-substituted quinoline compounds under the condition of the visible light with the photocatalyst.The possible mechanism and the application of this alkylation reaction of quinoline derivatives were also studied.The fourth chapter presents an efficient electrochemical method for the direct synthesis of complicated 1,3-diselenyl-dihydroisobenzofurans under external oxidant free conditions at room temperature from substituted o-divinylbenzenes and diselenides.The optimization of the reaction condition,the reaction mechanism and the application of the electrochemical reaction were studies.This thesis contains 78 figures,8 tables and 139 references.