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Photoelectrocyclization Reactions of Amidonaphthoquinones.

ABSTRACT: Readily available acrylamide naphthoquinones can be converted into the corresponding aza-anthraquinones using 6π-photoelectrocyclization reactions. Not only do these reactions not proceed thermally but, as demonstrated here, they can also be used to generate a range of aza-anthraquinone and aza-tetracycline derivatives including the natural products griffithazanone A and marcanine A. Several of the aza-anthraquinones generated in this work showed antibacterial activity.

SUBMITTER: Yin J

PROVIDER: S-EPMC7164668 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Photoelectrocyclization Reactions of Amidonaphthoquinones.

Yin Jinya J Landward Michael B MB Rainier Jon D JD

The Journal of organic chemistry 20200305 6

Readily available acrylamide naphthoquinones can be converted into the corresponding aza-anthraquinones using 6π-photoelectrocyclization reactions. Not only do these reactions not proceed thermally but, as demonstrated here, they can also be used to generate a range of aza-anthraquinone and aza-tetracycline derivatives including the natural products griffithazanone A and marcanine A. Several of the aza-anthraquinones generated in this work showed antibacterial activity. ...[more]

PMID: 32072812

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