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Review of 'Synthesis of Quinolinequinone Derivatives and related Carbocyclic Compounds'

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Buchwald-Hartwig amination for activated vinyl chlorides/bromides..
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Synthesis of Quinolinequinone Derivatives and related Carbocyclic Compounds

 Uchechukwu,  Thomas Wirth (corresponding) ,  Samuel Egu (2014)
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 transition-metal catalyzed arylations of 6,7-dibromo-5,8-quinolinequinone, 6,7-chloro-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.
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    Review information

    10.14293/S2199-1006.1.SOR-CHEM.AALL9P.v1.RJHIZB

    This work has been published open access under Creative Commons Attribution License CC BY 4.0, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Conditions, terms of use and publishing policy can be found at www.scienceopen.com.

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    Review text

    There is already cheaper method for the synthesis of 6-arylamino-7chloro-5,8 quinoline diones using CeCl3.7H20 from 6,7-dichloro-5,8-quinoline diones. Unfortunately the authors did not cite that article (Bioorg. Med. Chem. 2004, 12, 1623). The amination of 2,3-dichloro-1,4 napthoquinones by this strategy (Buchwald-Hartwig amination) is new and was not reported by older method. It will be interesting if the authors could also synthesize 7-arylamino-6chloro-5,8quinolinediones as their structures are similar to Streptogirin 2,3 and Lavendamycin4 (Figure 1).

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