| 4-Quinolone is a nitrogen-containing heterocyclic compound with good biological activity,widely present in many natural active products and biomedicine,and is widely used in the treatment of infectious diseases,tumors,malaria and AIDS and other diseases.Homogeneous gold catalysis is a convenient and quick a step method for obtaining complex and diverse molecules,but it is rarely applied in the synthesis of multi-substituted 4-quinolone.Therefore,in this paper,a series of multi-substituted4-quinolone was obtained through gold-catalyzed cyclization of azidoaryl propargyl alcohol substrate and the migration reaction initiated byα-imine gold carbene during the catalytic process.The specific research content mainly includes the following three aspects:（1）To realize the gold-catalyzed cyclization of azidoaryl propargyl alcohol substrate.The optimal reaction conditions were determined by screening the influencing factors.Such as,solvent,reaction temperature,gold catalyst and its loading.（2）Under the optimal reaction conditions,the universality of the reaction substrate is explored by changing the substituents at different positions of the substrate,obtained 26different multi-substituted 4-quinolone with a medium to high yield.The product structure was confirmed by 1H NMR,13C NMR,19F NMR and HRMS.（3）Explore synthetic applications of the reaction.First,the reaction was scaled up to the level of 1 mmol,and the yield was maintained well.Then the reaction was applied to synthesis 2-heptylquinolin-4（1H）-one,1,3-dimethyl-2-phenyl-4-quinolone and3,4-methoxy-3-methyl-2-phenylquinoline with medium to high yields.The availability of these biologically active substances shows that the reaction has certain application potential. |
