Abstract
4-Aminoacenaphthene (VI) was synthesized from 4-nitro-5-acetamidoacenaphthene (III) through 4-nitro-5-amino compound (IV) and reduction of 4-nitroacenaphthene (VI). (VI) was then derived to 4-acylamino (VII) and 4-thioacylamino (VIII) compounds, and oxidation of (VIII) with alkaline potassium ferricyanide afforded the cyclized product, thiazole compound. For this cyclized product, two isomers can be considered, 8-substituted 1, 2-dihydroacenaphtho [4, 3-d] thiazole (XII) and 4, 5-dihydroacenaphtho [4, 5-d] thiazole (XIII). In order to prove this structure, synthesis of (XIII) was attempted. (IV) was derived to 4-nitro-5-halo compound (IX) which was led to 4-nitro-5-thiol (X) or disulfide (XI) compound. Reduction of (X) or (XI) with zinc dust in acetic anhydride, followed by concurrent acetylation and dehydrative cyclization afforded the objective compound (XIII: R=CH3). It was thereby found that the above cyclized compound (VIII: R=CH3) is identical with the synthesized product, proving that the cyclized product from (XVIII) is (XIII). Ultraviolet and infrared absorption spectra of several kinds of acenaphthene compound were measured.
