2-(Fur-2-yl)thiazolo[4,5-f]quinoline: Synthesis and Electrophilic Substitution Reactions

Abstract

Condensation of quinoline-5-amine with furan-2-carbonyl chloride in propan-2-ol afforded N-(5- quinolyl)furan-2-carboxamide, treatment of which with an excess of P₂S₅ in anhydrous pyridine led to the formation of the corresponding thioamide. Oxidation of the latter with potassium ferricyanide in an alkaline medium furnished 2-(fur-2-yl)thiazolo[4,5-f]quinoline. A plausible mechanism for its formation was proposed. The reactions of electrophilic substitution (nitration, bromination, formylation, acylation) of the obtained N-(5-quinolyl)furan-2-carboxamide were studied.