Facile synthesis of 1-(arylimino)naphthalen-2(1H)-ones from anilines and 2-naphthols promoted by NaBr/K2S2O8/CAN

An efficient method has been developed for the synthesis of 1-(arylimino)naphthalen-2(1H)-ones through the cascade reaction of anilines and 2-naphthols promoted by NaBr/K2S2O8/Ce(NH4)2(NO3)6. Using this protocol, a series of 1-(arylimino)naphthalen-2(1H)-ones was obtained in good to excellent yields (17 examples, 70-92% yields). The reactions may proceed through the following steps: bromination of 2-naphthols by in-situ-generated bromine from NaBr and K2S2O8 to afford 1-bromonaphthalen-2-ols, coupling of 1-bromonaphthalen-2-ols with anilines to afford the corresponding amines, and subsequent oxidation of the amines into the products by Ce(NH4)2(NO3)6. These newly obtained α-imine ketones have great potentials for synthesis of special optical materials bearing naphthalene moiety.