A clean and simple method for the preparation of 2-(anilino)-1,4-naphthoquinones (PANs) is presented by the reaction of naphthoquinone (NQ)  and anilines under ultrasound irradiation (US). Anilino derivatives were synthesized in very good yields and shorter reaction times in comparison with the conventional method. This ultrasound procedure can be applied to the preparation of the naphthoquinone derivatives with anilines with donor substituentes (2-OMe, 4-OMe, 4-Me and 4-OEt ) and electron withdrawing and halogenated substituents (4-F, 4-Cl, 4-Br, 3-F, 3-Cl, 3-Br and 4-Ac). This procedure can also be applied to the reaction with anilines with 2,3-dichloro-1,4-naphthoquinone (DCNQ). A reaction mechanism involving an EDA complex is proposed based on NMR experiments and previous solid/solid reaction studies.

Green chemistry reaction of 1,4-naphthoquinonen with anilines through an EDA complex

254th National Meeting (2017)

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