Studies On The Three-component Reaction Of Arynes,Imines And α,β-unsaturated Compounds

Aryne has become a powerful synthon in organic synthesis because of its high reactivity.Unlike traditional aryl electrophiles such as aryl halides and pseudohalides,arynes can react with two reaction components in a sequential order.Such three-component reactions are widely used in the functionalization of various heterocyclic compounds and the synthesis of biologically active compounds.Nitrogen-containing heterocyclic compounds are important building blocks for many biologically active molecules.Among them,five-membered N-heterocycles and 1,4-disubstituted seven-membered heterocycles play an important role.Therefore,it is very meaningful to explore the synthesis of these two types of compounds.The high reactivity and efficient and preparative method of arynes render it great advantages in the synthesis of these two types of heterocyclic compounds.In this thesis,2-(trimethylsilyl)phenyl trifluoromethanesulfonate derivatives are used as the precursors of arynes.Without transition-metal-catalysis,the three-compotent reaction of imine derivatives,arynes and α,β-unsaturated compounds including acrylonitrile and ethyl acrylate are used to synthesize polysubstituted pyrrolidines,homopiperazines,homomorpholines,tetrahydroisoquinolines and dihydroquinolines.The three-component reactions are valuable beacause of the readily available substrates,mild condition and wide applicability.