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

✍ Scribed by Wentao Gao; Mingchun Sun; Yang Li

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 160 KB
• Volume: 28
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.201090241

✦ Synopsis

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). Compounds 3, 4, 6 reacted respectively with hydroxyamine to give the corresponding 3‐[2‐(1‐naphthyl)vinyl]‐8__H__‐cyclohepta[d]isoxazol‐8‐ones (9–11). The reactions of 3, 5 with phenylhydrazine and substituted phenylhydrazines gave 3‐[2‐(1‐naphthyl)vinyl]‐1‐phenylcyclohepta[c]pyrazol‐8(1__H__)‐ones (12–18).