Synthesis and reactivity of 2-(furan-2-yl)benzo[e][1,3]benzothiazole

N-(1-Naphthyl)furan-2-carboxamide was synthesized by the coupling of naphthalen-1-amine with furan-2-carbonyl chloride in propan-2-ol and then treated with excess P2S5 in anhydrous toluene to obtain the corresponding thioamide. The latter was oxidized with potassium ferricyanide in an alkaline medium by the Jakobson procedure to synthesize 2-(furan-2-yl)benzo[e][1,3]benzothiazole which was subjected to electrophilic substitution reactions: nitration, bromination, formylation, and acylation.