Abstract
An efficient method is described for the first time for reductive aza-Claisen rearrangement of 1-(N-allylamino)anthraquinones to 1-amino-2-(prop-2'-enyl)anthraquinones using zinc powder in 1-methylimidazolium tetrafluoroborate ([Hmim] BF4) as an ionic liquid in good to excellent yields. Extending of this method on 1-(N-propargylamino)anthraquinones causes the production of 1,2,3,4-tetrahydronaphtho[2,3-h]quinoline-7,12-diones containing a newly synthesized six membered heterocyclic ring on anthraquinone core via performing this reductive [3,3] sigmatropic reaction followed by cyclization in a tandem manner. These rearrangements can be executed even in the presence of some other functional groups with excellent chemoselectivity.
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