ChemInform Abstract: Functionalized Naphtho[2,3-h]quinoline-7,12-diones.

✍ Scribed by I. I. Barabanov; L. G. Fedenok; M. S. Shvartsberg

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199914170

✦ Synopsis

Functionalized Naphtho[2,3-h]quinoline-7,12-diones.

-Reaction of anthraquinonepropionate (III) with primary or secondary amines (IV) affords a 4:1 mixture of regioisomeric addition products. Whilst the minor adduct cyclizes in situ to furnish naphthoquinolinediones (VI), the stable major adduct (V) cyclizes on treatment with POCl 3 , sulfuric acid or under phase-transfer catalysis conditions providing access to several 2-functionalized naphthoquinolinediones (VII), (X), and (XI). The 2-chloro derivative (VII) represents a synthetic useful precursor for several further 2-substituted naphthoquinolinediones (IX) as shown by nucleophilic substitution of chlorine by piperidino, butylthio or di(ethoxycabonyl)methyl group. -(BARABANOV, I. I.; FEDENOK, L. G.;