Synthesis, spectral and electrochemical characterization of novel 2-(fluoroanilino)-1,4-naphthoquinones

The preparation of novel 2-(fluoroanilino)-1,4-naphthoquinones is presented. It takes place under mild conditions by reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl3·7H2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV–Vis, IR, 1H and 19F NMR, MS and cyclic voltammetry, to investigate the effect of the fluoro-substituents on their electronic properties.

Graphical abstractNovel 2-(fluoroanilino)-1,4-naphthoquinones were prepared reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl3·7H2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV–Vis, IR, 1H and 19F NMR, MS and cyclic voltammetry.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights▶ Synthesis and characterization of 2-(fluoroanilino)-1,4-naphthoquinone. ▶ Synthesis of naphthoquinone derivatives with Lewis catalysts and oxidizing agents. ▶ The synthesis was also carried out under microwave irradiation. ▶ Compounds were characterized by UV–Vis, 1H and 19F NMR, M.S. and electrochemistry.