Synthesis and Reactions of Halo‐, Arylazo‐substituted 3‐(3‐(1‐naphthyl)acryloyl)tropolones. Formation of (Naphthalen‐1‐yl)vinyl)substituted Heterocycle‐fused Troponoid Compounds

Abstract

The starting substrate 3-(3-(1-naphthyl)acryloyl)tropolone (3) was achieved by the aldol condensation reaction of 3-acetyltropolone with 1-naphthaldehyde. Compound 3 reacted with bromine to afford 7-bromo-3-(3-(1-naphthyl)acryloyl)tropolone (4), 5,7-dibromo-3-(3-(1-naphthyl)acryloyl)tropolone (5) according to the molar ratio of the reactants. Iodination of 3 gave 7-iodo-3-(3-(1-naphthyl)acryloyl)tropolone (6). Azo-coupling reactions of 3 gave the 5-arylazo-3-(3-(1-naphthyl)acryloyl)tropolones (7-8