Zinc-mediated efficient and selective reductive aza-Claisen rearrangement of N-allyland N-propargylaminoanthraquinones in ionic liquid

An efficient method is described for the first time 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 good excellent yields. Extending this on 1-(N-propargylamino)anthraquinones causes production 1,2,3,4-tetrahydronaphtho[2,3-h]quinoline-7,12-diones containing a newly synthesized six membered heterocyclic ring anthraquinone core via performing [3,3] sigmatropic reaction followed by cyclization tandem manner. These rearrangements can be executed even presence some other functional groups with chemoselectivity.