Synthesis of Novel Thio-Substituted Aminonaphthoquinones

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 variousthiol 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 byapplying a method published in literature. Finally, obtained novel compounds (5a-5f) were characterized via IR, 1H NMR, 13CNMR, and MS techniques. Based on previous studies in the literature, it is expected that some potential biological activities ofnew compounds could find application in medicinal chemistry.