Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones.

Org Lett

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.

Published: April 2013


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Article Abstract

A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (S(E)Ar) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

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http://dx.doi.org/10.1021/ol400371hDOI Listing

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