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

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. © 2015 Published by Elsevier Ltd.

2-(2 4-Dinitroanilino)-1 4-naphthoquinone; CeCl3·7H2O; Lewis acid catalyst 1,4 naphthoquinone derivative; 2 (2 fluorophenylamine) 3 (2,4 dinitrophenylamine) 1,4 naphthoquinone; 2 (2 methoxyaniline) 3 (2,4 dinitrophenylamine) 1,4 naphthoquinone; 2 (3 fluorophenylamine) 3 (2,4 dinitrophenylamine) 1,4 naphthoquinone; 2 (3,4 difluorophenylamine) 3 (dinitrophenylamine) 1,4 napthoquinone; 2 (4 flourophenylamine) 3 (2,4 dinitrophenylamine) 1,4 naphthoquinone; 2 (fluoroanilino) 3 (2,4 dinitroanilino)derivative; aniline derivative; chlorine; Lewis acid; unclassified drug; Article; atom; catalyst; drug synthesis; electron; nitration; nuclear magnetic resonance; nucleophilicity; reaction time

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