Cobalt-catalyzed Perfluoroalkylation Of Quinolineamides At The C5 Position

8-aminoquinoline is an important structure,its C5-derivatives are widely used in pharmaceuticals and chemical analysis.In this thesis,a series of quinolineamide substrates were synthesized.The cobalt-catalyzed perfluoroalkylation of quinolineamides at the C5 position were achieved.Various 8-aminoquinoline amides could be smoothly converted to corresponding products.On the basis of relevant literatures and experimental results,a plausible mechanism was proposed.This protocol provided a new and efficient method to synthesize perfluoroalkyled 8-aminoquinoline amide derivatives.The main research results are shown as follows:1.Synthesis of 8-aminoquinoline amidesA series of benzoic acids and fatty acids bearing various substituents were converted to acyl chlorides.Then the condensation reaction between 8-aminoquinoline and acyl chloride was performed,affording corresponding 8-aminoquinoline amides in 52-87% yields.2.Cobalt-catalyzed perfluoroalkylation of quinolineamides at the C5 positionTo optimize the reaction conditions,1a and 2a were employed as template substrate and perfluoroalkyl source,respectively.The optimal conditions were as follows: Co(acac)3(5 mol%),Ag2O(1.0 equiv.),HOAc(2.0 equiv.),DCM(1.0 m L),air,at 120 oC for 4 h.Under the optimal conditions,the substrate scope was extended.Perfluoroalkyl groups were introduced into a series of 8-aminoquinolin amides in 47-84% yields with 28 examples in total(Scheme 2).