Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives

Abstract

In this study, some new sulfanyl-substituted amino 1,4-naphthoquinone derivatives which possess two electron-donating groups in the amino fragment were synthesized and their structures were analyzed by spectroscopic techniques. First, 2-chloro-3-[(2,4dimethoxyphenyl)amino]naphthalene-1,4-dione (3a) and 2-chloro-3-[(3,5dimethoxyphenyl)amino]naphthalene-1,4-dione (3b) were obtained from the reactions of dichloro-1,4-naphthoquinone (1) with 2,4-dimethoxyaniline and 3,5-dimethoxyaniline. In the following step, the compounds 3a,b were reacted with aliphatic nucleophiles; ethyl-, 1-propyl-, and 1-pentyl mercaptan. S-nucleophiles attacked the carbon atom of 1,4-naphthoquinone core and displaced the chlorine atom to create target molecules; 2-arylamino-3-(ethylthio)naphthalene-1,4-dione (5a,b), 2-arylamino-3-(propylthio)naphthalene-1,4-dione (5c,d), 2-arylamino-3-(pentylthio)naphthalene-1,4-dione (5e,f) derivatives. The structures of the synthesized compounds were elucidated by utilizing 1D and 2D NMR techniques with additional spectroscopic data (mass and FTIR).

Synthesis of Novel Thio-Substituted Aminonaphthoquinones

“…Recently, sulfanyl and trifluoromethyl containing aryl amine substituted 1,4-naphthoquinones have been synthesized and characterized successfully [46][47][48]. The different influences of the -CF 3 group position in aryl amine ring of the newly prepared compounds were clearly elucidated and the molecular docking studies have also supported the experimental results.…”