Cobalt-catalyzed C-H Benzylatian Of 8-aminoquinolines On C5 Position

In this thesis,a variety of 8-aminoquinoline amides were synthesized.The first cobalt-catalyzed benzylatian of aminoquinolines on the C5 position was developed.A broad range of aminoquinoline amide substrates bearing various functional groups were well tolerated.This protocol provides a facile access to the benzyl substituted quinolones.The main research results are shown as follows:1.The synthesis of 8-aminoquinoline substrates8-aminoquinoline substrates were obtained by the reaction of the corresp~onding acyl chloride with 8-aminoquinoline(1.1 equiv.)in the reaction conditions:1,2-dichloroethane as solvent,triethylamine as base,0 ? for overnight under air atmosp~here.(Scheme 1).2.Cobalt-catalyzed C-H benzylatian of 8-aminoquinolines on C5 positionFirstly,the C(sp~2)-H/C(sp~3)-H cross-coupling of the quinolineamide 1a with butylated hydroxytoluene(BHT)2a was chosen as the model reaction,then the cobalt salt,base,oxidant,solvent were screened.The desired products could be obtained in 88% yield,when the reaction underwent with the optimal reaction condition: Co(OAc)2·4H2O(20 mol%),Ag TFA(2.0 equiv.),120 ? for 12 h at air atmosp~here(Scheme 2).Both armatic and aliphatic amides could be well tolerated to generate the corresp~onding products.The reaction provided the benzyl products yields from 50% to 98% with 26 examples in all.