Issue 2, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
17 Oct 2018
Accepted
27 Nov 2018
First published
28 Nov 2018

Org. Chem. Front., 2019,6, 195-204

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, 6, 195 DOI: 10.1039/C8QO01121D

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