8-(furan-2-yl)-4,5-dihydroacenaphtho[5,4-d]thiazole. Synthesis and reactions of electrophilic substitution

Abstract

Condensation of 1,2-dihydroacenaphthylen-5-amine with furoyl chloride in 2-propanol afforded N-(1,2-dihydroacenaphthylen-5-yl)furan-2-carboxamide, whose treatment with excess P₂S₅ in anhydrous toluene led to the formation of the corresponding thioamide, and the oxidation with potassium ferricyanide in alkaline medium by Jacobson procedure resulted in 8-(furan-2-yl)-4,5-dihydroacenaphtho[5,4-d]thiazole. The latter was brought into electrophilic substitution reactions: nitration, bromination, formylation, acylation. Depending on the reaction conditions either the furan ring or the acenaphthene fragment suffer the attack.