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

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/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.

Graphical Abstract

KEYWORDS:

• Anilines
• cerium(IV) diammonium nitrate
• potassium persulfate
• 1-(arylimino)naphthalen-2(1H)-ones
• 2-naphthols

Additional information

Funding

We gratefully acknowledge the National Natural Science Foundation of China [No. 21242013] for financial support.