Study On The Reaction Of Palladium Catalyzed Isocyanides And Phenylboronic Acids In The Synthesis Of Quinazolinones

In the past decades,intensive studies have been conducted on the insertion of isocyanides between carbon-halogen bonds and carbon-hydrogen bonds.However,there are few reports on the insertion of isocyanides as C1 building blocks into carbon-boron bonds.To investigate whether oxidative three-component coupling of isocyanides as C1 building blocks with aromatic boronic acids and anthranilamides could be used to synthesize nitrogen-containing heterocyclic quinazolinones,which will expand their applications synthesis of compounds with biological activity.By screening the factors that affected the reaction,such as catalyst,ligand,oxidant,solvent,etc.,to find the optimal reaction conditions for synthesis of 2,3-disubstituted quinazolinones via palladium-catalyzed oxidative three-component coupling of isocyanides with anthranilamides and arylboronic acids.The optimal reaction conditions for the synthesis of2,3-disubstituted quinazolinones by oxidative palladium-catalyzed reaction involving isocyanide insertion into carbon-boron bonds are arylboronic acid,isocyanide,anthranilamide,Pd?PPh₃?₂Cl₂,anhydrous Cu?OAc?₂,and anhydrous DMF.Inthispaper,we overcame the problem of direct oxidative coupling of arylboronic acid and anthranilamide in the presence of metallic copper,and achieved oxidative three-component coupling of isocyanides as C1building blocks with anthranilamides and arylboronic acids to synthesize nitrogen-containing heterocyclic quinazolinones with biological activity.