The Radical Addition Of Carbon-carbon Double Bonds In Tandem Cyclization To Synthesize Nitrogen And Oxygen Heterocyclic Compounds

By the addition of radicals to carbon-carbon double bonds,various functional groups with complex functions can be added or synthesized,such as trifluoromethylation to introduce fluorine groups,sulfonylation to introduce sulfonyl groups,or tandem reactions for more complex fused ring compounds and so on.In this thesis,we introduce new methods to synthesize alkylated oxygen-containing heterocycles and deuterated nitrogen-heterocyclic compounds by the tandem addition reaction of radicals with carbon-carbon double bonds.The main content of the thesis is as follows:1.BPO promotes the C?sp³?-H functionalization reaction of diaryl vinyl ether and non-activated alkaneUsing 2-?Vinyloxy?-1,1?-biphenyl as a substrate,cyclohexane forms alkyl radicals under peroxide conditions,and adds to carbon-carbon double bond,6-Alkyl-6H-benzo[c]chromene compound is synthesized by tandem cyclization and aromatization.This reaction uses cheap and readily available non-activated alkane as the source of alkyl radical and solvent,and the reaction is compatible with various substituents on the benzene ring.In addition,using vinyl thioethers as a raw material,the corresponding6H-benzo[c]thiochromene derivatives can also be synthesized well.2.Iron-mediated deuterium radical addition cascade cyano insertion/cyclization of N?arylacrylamides to access deuterium-labelled phenanthridinesThe readily available iron salt Fe?NO₃?₃·9H₂O and Na BD₄ or Na BH₄ are used to generate deuterium or hydrogen radicals,and free radical adds to the terminal olefin of N-arylacrylamide.Next,the addition of a new radical to the cyano group forms the imine radical.Finally,after cyclization and aromatization,we obtain a phenanthridine compound.Some N-arylacrylamide substituted with various electron-donating groups,electron-withdrawing groups and even reduction-sensitive groups have good yields to obtain deuterated phenanthridine compounds,which have potential application in drug synthesis.