Synthesis of quinolinequinone derivatives and related carbocyclic compounds

Abstract

Palladium-catalyzed Buchwald-Hartwig aminations of various quinolinequinone derivatives give excellent yields of novel 6-arylamino derivatives of the disubstituted quinolinequinones and 3-arylamino derivatives of the corresponding naphthoquinones. The precursor quinolinequinones are prepared in a three-step sequence from 8-hydroxyquinoline. The transitionmetal-catalyzed arylations of 6,7-dibromo-5,8-quinolinequinone, 6,7-dichloro-5,8-quinolinequinone and 2,3-dichloro-1,4-naphthoquinone are reported for the first time and offer fast and easy access to their derivatives.

Synthesis of Amino Acid and Aniline Derivatives of Quinolinediones

“…Despite the several modifications, the Chemistry of quinolinediones remains poorly developed [4]. Furthermore, nitrogen, oxygen and sulphur containing compounds are known to be essentially used in medicine for the treatment of different infections and ailments [5], because of their high efficiency against diseases [6].…”

“…As a result of the aforementioned and extension of our interest in the synthesis of quinolinedione derivatives [8,9,10], this research reports synthesis of amino acid and aniline derivatives of quinolinediones with the hope of obtaining compounds of improved activities and new areas of applications.…”

“…Since then, they have been an area of interest to large number of researchers because of their vast spectrum of bioactivities, like potent antifungal, antibacterial [2], antimalarial [3] and antineoplastic [4] properties. Since the discovery of quinolinedione, several variations have been done to it not only to obtain molecules of enhanced properties, but also to find new scope of applications [4]. As a result, modifications in the parent structure have resulted in a good…”