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… Click to show full 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.
               
Click one of the above tabs to view related content.