Solvent Interception Of Catalytic Generated Carbene Intermediate With Azide-Tethered Ynones:Expeditious Synthesis Of Quinoline Derivatives

As a reactive intermediate,metal carbene plays an important role in organic synthetic chemistry.This species is usually obtained by catalytic decompostion of diazo compounds.The synthetic applications and selectivity controls are the main challenges in the carbene chemistry.Therefore,the development of new sustainable and safe alternatives has become a top issue for chemists.In recent years,alkyne,as a stable and readily available carbene precursor,has attracted chemists' attentionThe first chapter introduces the researches on the catalytic functionalization of alkynes,the design of the research project,and main content of this thesisThe second chapter introduces the silver-catalyzed cyclization reaction of azide-tethered alkynes to construct polysubstituted quinoline compounds.This work reported a silver-catalyzed 6-endo-dig cyclization of azide-tethered alkynes,which generated the key ?-imino carbene intermediate.The carbene intermediate is then captured by the halide through a R-X insertion reaction to form polysusbtituted quinoline derivativesThe third chapter describes the study of a gold-catalyzed cyclization of azide-tethered alkynes to construct oxazolo[4,5-c]quinolines.Based on the above research,we find that nitriles,as a weak nucleophile,can undergo[2+3]cycloaddition reaction with the in situ generated ?-imino carbene intermediate,delivering the oxazolo[4,5-c]quinoline derivatives in high yields under mild reaction conditionsIn this thesis,the azide-tethered ynones are catalyzed by gold or silver to form the key carbene intermediate through a 6-endo-dig cyclization process and then obtain polysubstituted quinoline derivatives through the metal carbene R-X insertion and[3+2]-cycloaddition with the corresponding solvents.