Study On The Synthesis Of Benzylamine Substituted Tetrahydrofurans Under UV

Tetrahydrofuran(THF)is an organic heterocyclic compound which containing an oxygen atom in its skeleton.THF moiety widely exists in drug molecules and natural products,such as the famous drugs gemcitabine,apronavir,sofibuprovir,and the natural products of lycopene.The structure of benzylamine also exists in the skeleton of many drug molecules.Therefore,the studied on the synthesis of substituted THFs and benzylamine compounds are of the important fields in drug development.The activation of C-H bonds for further transformations is an important field in the research of modern synthesis,and it is an indispensable technical support for the efficient construction of drug molecules.Many synthesis methods based on the activation of C-H bonds have been used in the synthesis of drug molecules.The direct synthesis of substituted THFs based on the activation THF C(sp~3)-H is scientifically important and has applicable value for the synthesis of THF-contained drugs and biologically active compounds.The C(sp~3)-H bond in THF is relatively stable in ordinary polar reactions.Thus,it is widely used as an organic solvent.The aim of this dissertation is to develop a facile method for direct fuctionalization of THF C(sp~3)-H bonds.Due to the stabilization of oxygen atom,theα-C(sp~3)-H bond of oxygen atom in THF can be oxidized to form an THF radical,which provides a possibility for the functionalization of THF directly through the radical pathway.In the dissertation,we have established a green synthesis method for the preparation of benzylamine substituted THFs,which laid a foundation for further drug research.Under the ultraviolet light irradiation,diarylketone catalyzed the addition of THFα-carbon radical to imines,and successfully realized the direct conversion of THF C(sp~3)-H bond to synthesized a series of benzylamine substituted THFs.In the study,various phenyl imine substrates worked well and gave the desired products in moderate to good yields.The preliminary mechanistic study suggested that a radical pathway was involved in the reactions.