Issue 5, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
03 mar 2017
Accepted
04 apr 2017
First published
05 apr 2017

Org. Chem. Front., 2017,4, 871-875

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, 4, 871 DOI: 10.1039/C7QO00172J

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