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Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

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Abstract

The bidentate bisborane Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction of 1,4-naphthoquinones (1,4-NQs) with 1,2,4,5-tetrazine (TZ) has been developed for the synthesis of 2,3-diaza-anthraquinones (2,3-DAAQs). Only due to the coordination of TZ with the bisborane catalyst, the IEDDA reaction of electron-deficient 1,4-NQs is possible. The use of TZ as the nitrogen source provides an efficient strategy to the 2,3-diaza-anthraquinones. The 2,3-DAAQs themselves are suitable dienes for a second bidentate Lewis acid catalysed IEDDA reaction with various dienophiles to afford substituted AQs. AQs have been discussed as privileged structures for applications in medicinal as well as materials science.

Graphical abstract: Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

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Publication details

The article was received on 03 Mar 2017, accepted on 04 Apr 2017 and first published on 05 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00172J
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

    L. Hong, S. Ahles, M. A. Strauss, C. Logemann and H. A. Wegner, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00172J

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