Synthesis of Novel Thio-Substituted Aminonaphthoquinones

Authors : Mahmut YILDIZ, Amaç Fatih Tuyun

Pages : 179-184

Doi:10.21541/apjes.373934

View : 13 | Download : 9

Publication Date : 2018-08-03

Article Type : Research Paper

Abstract :Novel thio-substituted aminonaphthoquinones were synthesized by the reactions of 2-(4-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3a) and 2-(3-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3b) with various thiol compounds such as ethanethiol (4a), methyl 2-mercaptoacetate (4b), ethyl 2-mercaptoacetate (4c). 2,3-dichloro-1,4-naphthoquinone (1) was reacted with aryl amines (2a, 2b) containing trifluoromethyl group to give compounds 3a and 3b by applying a method published in literature. Finally, obtained novel compounds (5a-5f) were characterized via IR, 1H NMR, 13C NMR, and MS techniques. Based on previous studies in the literature, it is expected that some potential biological activities of new compounds could find application in medicinal chemistry.
Keywords : CF3, Aminonaphthoquinone, 1, 4 naphthoquinone, thiol, aryl amine, trifluoromethyl group, electron withdrawing group, nucleophilic substitution