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- Title
Zinc-mediated efficient and selective reductive aza-Claisen rearrangement of N-allyland N-propargylaminoanthraquinones in ionic liquid.
- Authors
ALBOOYEH, Fereshteh; AGHAPOUR, Ghasem
- 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.
- Subjects
IONIC liquids; ZINC powder; ANTHRAQUINONES; FUNCTIONAL groups; CHEMOSELECTIVITY; TETRAFLUOROBORATES
- Publication
Turkish Journal of Chemistry, 2023, Vol 47, Issue 3, p514
- ISSN
1300-0527
- Publication type
Article
- DOI
10.55730/1300-0527.3557