Synthesis and Antioxidant Activity of Some Benzoquinoline-Based Heterocycles Derived from 2-((3-Chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide

Abstract

Abstract A new series of benzoquinoline-based heterocycles was synthesized utilizing the building block synthon, 2-((3-chlorobenzo[ f ]quinolin-2-yl)methylene)hydrazine-1-carbothioamide via the condensation of 3-chlorobenzo[ f ]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon-centered electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro- N -phenylacetamide, and dimethyl but-2-ynedioate to achieve triazolethione, imidazolone, thiazolidinone, and thiazole derivatives. In turn, the hydrazinolysis of this substrate did not proceed as expected but it afforded the azine derivative. The antioxidant activity screening of the produced compounds revealed that thiazole and triazolethione derivatives were the most potent.