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Synthesis of azulenophthalimides by phosphine-mediated annulation of 1,2-diformylazulenes with maleimides

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Abstract

The reaction of 1,2-diformylazulenes with several maleimides in the presence of PPh3 gave the corresponding azulenophthalimides with an ester function at the five-membered ring in moderate to good yields. The removal of the ester function from the azulenophthalimide with an N-cyclohexyl function was also achieved by the treatment with 100% H3PO4. The optical and electrochemical properties of the azulenophthalimides were investigated by UV/Vis measurements, voltammetry experiments and DFT calculations. The azulenophthalimide without the ester function exhibited remarkable emission under acidic conditions. Moreover, the azulenophthalimides displayed a significant spectral change under electrochemical reduction conditions.

Graphical abstract: Synthesis of azulenophthalimides by phosphine-mediated annulation of 1,2-diformylazulenes with maleimides

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Publication details

The article was received on 17 Oct 2018, accepted on 27 Nov 2018 and first published on 28 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO01121D
Citation: Org. Chem. Front., 2019, Advance Article
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    Synthesis of azulenophthalimides by phosphine-mediated annulation of 1,2-diformylazulenes with maleimides

    T. Shoji, T. Araki, N. Iida, K. Miura, A. Ohta, R. Sekiguchi, S. Ito and T. Okujima, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01121D

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