Ultrasound-assisted reaction of 1,4-naphthoquinone with anilines through an EDA complex
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Abstract: Naphthoquinone amino derivatives exhibit interesting physicochemical properties and a wide range of biological activities with potential medicinal applications. A clean, fast and simple method for the preparation of phenylamino-1,4-naphthoquinones is presented by the reaction of naphthoquinone (NQ) and anilines under ultrasound irradiation (US). Anilino derivatives were synthesized in good yields and shorter reaction times in comparison with the conventional method. This ultrasound procedure can be applied to the preparation of naphthoquinone derivatives with anilines containing electron-donor substituents (2-OMe, 4-OMe, 4-Me and 4-OEt) or halogen or electron-withdrawing substituents (4-F, 4-Cl, 4-Br, 3-F, 3-Cl, 3-Br, 4-Ac). This procedure was also applied to the reaction of anilines with 2,3-dichloro-1,4-naphthoquinone (DCNQ). A reaction mechanism involving an EDA complex is proposed based on NMR experiments and previous studies about solid/solid reactions. Graphical Abstract: [Figure not available: see fulltext.] © 2018, Springer International Publishing AG, part of Springer Nature.
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1, 4-Naphthoquinone; EDA complex; Nucleophilic substitution; Ultrasound 1,4 naphthoquinone; 2 (2 methoxyphenylamino) 1,4 naphthoquinone; 2 (3 bromophenylamino) 1,4 naphthoquinone; 2 (3 chlorophenylamino) 1,4 naphthoquinone; 2 (3 fluorophenylamino) 1,4 naphthoquinone; 2 (4 acetylphenylamino) 1,4 naphthoquinone; 2 (4 bromophenylamino) 1,4 naphthoquinone; 2 (4 chlorophenylamino) 1,4 naphthoquinone; 2 (4 ethoxyphenylamino) 1,4 naphthoquinone; 2 (4 fluorophenylamino) 1,4 naphthoquinone; 2 (4 methoxyphenylamino) 1,4 naphthoquinone; 2 (4 methylphenylamino) 1,4 naphthoquinone; 2 (4 nitrophenylamino) 1,4 naphthoquinone; 2 (phenylamino) 1,4 naphthoquinone; 2 chloro 3 (2 methoxyphenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 bromophenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 chlorophenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 ethoxyphenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 fluorophenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 iodophenylamino) 1,4 naphthoquinone; 2 chloro 3 (4 methoxyphenylamino) 1,4 naphthoquinone; 2 chloro 3 (phenylamino) 1,4 naphthoquinone; aniline derivative; edoxudine; unclassified drug; 1,4-naphthoquinone; aniline derivative; naphthoquinone; Article; controlled study; Fourier transform infrared spectroscopy; melting point; nucleophilicity; physical chemistry; priority journal; proton nuclear magnetic resonance; reaction time; regioselectivity; stereochemistry; thin layer chromatography; ultrasound; chemistry; Aniline Compounds; Naphthoquinones; Ultrasonic Waves
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