Synthesis of 2,6-Aceanthrylenedione, a Cyclic Vinylog of Anthraquinone

Synthesis of 2,6-Aceanthrylenedione, a Cyclic Vinylog of Anthraquinone

The first synthesis of 2,6-aceanthrylenedione (6), a cyclic vinylog of anthraquinone and a useful starting material for the synthesis of 1-phenylaceanthrylene-2,6-diones such as 7, 8, and 9, is described. (10-Oxo-10H-anthracen-9-ylidene) acetyl chloride (5) cyclizes intramolecularly at room temperat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2010-06, Vol.75 (11), p.3867-3870
Hauptverfasser: Prinz, Helge, Böhm, Konrad J, Müller, Klaus
Format: Artikel
Sprache:eng
Schlagworte:
Anthracenes - chemistry
Anthraquinones - chemical synthesis
Chemistry
Condensed benzenic and aromatic compounds
Cyclization
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Tubulin Modulators
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The first synthesis of 2,6-aceanthrylenedione (6), a cyclic vinylog of anthraquinone and a useful starting material for the synthesis of 1-phenylaceanthrylene-2,6-diones such as 7, 8, and 9, is described. (10-Oxo-10H-anthracen-9-ylidene) acetyl chloride (5) cyclizes intramolecularly at room temperature in the presence of AlCl3 to give 6. We found that 6 is a cytotoxic compound that inhibits tubulin polymerization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1003983