Synthesis and Characterization of Nitrogen and Sulfur Containing 1,4-Naphthoquinones

Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted

“…Similarly, 2,3,5,6-tetrachloro-1,4-benzoquinone 15 with various amine nucleophiles was investigated. As shown in Scheme 1, the reaction of 1 with different amines 2a, 2c, 2d, 2e, 2f, 2 g in ethanol in the presence of Na 2 CO 3 gave known and unknown compounds 3a [16,17], 3c, 3d, 3f, 3g [18], 4e. Compound 6b [19] obtained the reaction of 1 with 5b.…”

“…In the second step of this study, different molar amount of N-substituted naphthoquinone compounds 9 [16,21], 13 [16,23] was reacted with sodium azide in DMF. The phenazine compounds 11 and 14 [22] were synthesized and compound 11 has not yet been described in the literature (Scheme 2).…”

“…After the solvent was evaporated, the residue was purified by column chromatography on silica gel. [16,17]. Compound 3a was synthesized from aniline 2a (0.4 ml, 4.404 mmol) and 2,3-dichloro-1,4-naphthoquinone 1 (1 g, 4.404 mmol) according to the general method.…”

“…Compound 7a was synthesized from ethanethiol 5a (0.110 ml, 1.762 mmol) and 2-chloro-3-(phenylamino) naphthalene-1,4-dione 3a (0. [16,21]. [22]).…”

“…After the solvent was evaporated, the residue was purified by column chromatography on silica gel. [16,23]. Dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione (17).…”