Journal article

Publication year: 2017

Pages: 871-875

Journal: Organic Chemistry Frontiers

Volume number: 4

Issue number: 5

ISSN: 2052-4129

DOI Link: https://doi.org/10.1039/c7qo00172j

Publisher: Royal Society of Chemistry

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 2,3diaza- 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.

Harvard Citation style: Hong, L., Ahles, S., Strauss, M., Logemann, C. and Wegner, H. (2017) Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electrondemand Diels-Alder (IEDDA) reaction dagger, Organic Chemistry Frontiers, 4(5), pp. 871-875. https://doi.org/10.1039/c7qo00172j

APA Citation style: Hong, L., Ahles, S., Strauss, M., Logemann, C., & Wegner, H. (2017). Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electrondemand Diels-Alder (IEDDA) reaction dagger. Organic Chemistry Frontiers. 4(5), 871-875. https://doi.org/10.1039/c7qo00172j