Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone

• Published in: Tetrahedron letters Vol. 56; no. 37; pp. 5248 - 5251
• Main Authors: Leyva, Elisa, Baines, Kim M., Espinosa-González, Claudia G., López, Lluvia I., Magaldi-Lara, Diego A., Leyva, Socorro
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.09.2015; Elsevier
• Subjects: 2-(2,4-Dinitroanilino)-1,4-naphthoquinone; CeCl3·7H2O; Chemistry; Chemistry, Organic; Lewis acid catalyst; Physical Sciences; Science & Technology; CeCl3·7H2O; Lewis acid catalyst; 2-(2,4-Dinitroanilino)-1,4-naphthoquinone; POTENT ANTIFUNGAL; PYRIDINE; ANTIBACTERIAL AGENTS; CeCl3 center dot 7HO; QUINONE CHEMISTRY; 2,3-DICHLORO-1,4-NAPHTHOQUINONE; BIOLOGICAL EVALUATION; NITROGEN; SULFUR-CONTAINING HETERO-1,4-NAPHTHOQUINONES; CYTOTOXICITY; WATER
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.07.046

[Display omitted] •A facile preparation of novel 2-(fluoroanilino-)-3-(2,4-dinitroanilino)-1,4-naphthoquinone derivatives is presented.•2-Anilino-3-chloro-1,4-naphthoquinone was prepared in quantitative yields utilizing a Lewis acid with good oxidation properties like CeCl3·7H2O. This compound was nitrated.•2-Chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone reacted with weakly nucleophilic fluoro anilines.•The 1H and 13C NMR signals were assigned using two dimensional NMR techniques (COSY, gHSQC, and gHMBC).•Synthesis and NMR of 2-(fluoroanilino-)-3-(2,4-dinitroanilino)-1,4-naphthoquinones. Several novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone have been synthesized in good to excellent yields. First, 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone was prepared in two steps beginning with the reaction of 2,3-dichloro-1,4-naphthoquinone with aniline in the presence of a Lewis acid (CeCl3·7H2O). The resulting 2-(anilino)-1,4-naphthoquinone was then nitrated. The strong electron withdrawing effect of the 2,4-dinitroanilino substituent on the naphthoquinone framework facilitated the displacement of the second chlorine atom by a variety of weakly nucleophilic fluoro-substituted anilines under reflux conditions.