Abstract
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/K
2
S
2
O
8
/Ce(NH
4
)
2
(NO
3
)
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 K
2
S
2
O
8
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(NH
4
)
2
(NO
3
)
6.
These newly obtained α-imine ketones have great potentials for synthesis of special optical materials bearing naphthalene moiety.