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.
N-Allylaminoanthraquinone, N-propargylaminoanthraquinone, zinc powder, reductive aza-Claisen rearrangement, ionic liquid
ALBOOYEH, FERESHTEH and AGHAPOUR, GHASEM
"Zinc-mediated efficient and selective reductive aza-Claisen rearrangement of N-allyland N-propargylaminoanthraquinones in ionic liquid,"
Turkish Journal of Chemistry: Vol. 47:
3, Article 2.
Available at: https://journals.tubitak.gov.tr/chem/vol47/iss3/2