Thenovel naphtho[1,2-g]indole and naphtho[2,1-g]indole containing azo dyes have been synthesized in the non-polar organic media under phase transfer catalysis. Obtained disperse dyes are suitable for dyeing nylon and polyester fibers from light yellow to red color with good-excellence dyeing levelness, light, washing and sublimation fastness. Additionally, the quantum-chemical calculations have been performed using quantum mechanical (MM2) and semi-empirical (AM1) methods, which allow to predict the activity of dyes against AhR ligand.