Rh(III)‐Catalyzed C−H Activation of 2‐Aryl Quinazolinones and Coupling with 2‐Carboxyl Allylic Alcohols for the Synthesis of β‐Aryl Ketone Substituted Quinazolinones

An efficient method to access 2‐(2‐β‐aryl ketone) substituted 2‐arylquinazolinones is reported. 2‐Carboxyl allylic alcohols, which were readily available from the Morita‐Baylis‐Hillman adducts, were used as the synthons. The reaction between 2‐aryl quinazolinones and 3‐hydroxy‐2‐methylene‐5‐phenylpentanoic acid was catalyzed by [RhCp*Cl2]2‐CF3COOAg through C−H activation and underwent facile decarboxylation to give the corresponding 2‐(2‐β‐aryl ketone) substituted 2‐phenyl quinazolinones in good to excellent yields with a wide range of substrates tolerated and good group compatibility. The results of control experiments indicated that the nitrogen atom on 3‐position of quinazolinone skeleton may function as the directing group in this C−H activation/functionalization. A possible mechanistic pathway for the synthesis of 2‐(2‐β‐aryl ketone) substituted phenylquinazolin‐4(3H)‐ones is proposed An efficient strategy for access 2‐(2‐β‐aryl ketone) substituted 2‐arylquinazolinones was described. The reaction bewteen 2‐aryl quinazolinones and 2‐carboxyl allylic alcohols was catalyzed by [RhCp*Cl2]2‐CF3COOAg through C−H activation and underwent facile decarboxylation, to give the corresponding 2‐(2‐β‐aryl ketone) substituted phenyl quinazolinones in good to excellent yields with broad substrate tolerance and good group compatibility.