Syntheses and reactions of halo- and arylazo-substituted 3-(3-(2-naphthyl)acryloyl)tropolones: Formation of (naphthalen- 2-yl)vinyl)-substituted heterocycle-fused troponoid compounds

✍ Scribed by Wentao Gao; Mingchun Sun; Yang Li; Wei Li; Kimiaki Imafuku

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 113 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.243

✦ Synopsis

Abstract

magnified image The starting substrate 3‐(3‐(2‐naphthyl)acryloyl)tropolone (1) was achieved by the aldol condensation reaction of 3‐acetyltropolone with 2‐naphthaldehyde. Compound (1) reacted with bromine to give 7‐bromo‐(2) and 5,7‐dibromo‐3‐(3‐(2‐naphthyl)acryloyl)tropolone (3) according to the amount of the brominated reagent. Iodination of 1 gave 7‐iodo‐3‐(3‐(2‐naphthyl)acryloyl)tropolone (4). Azo‐coupling reactions of 1, 2, and 4 gave 5‐arylazo‐3‐(3‐(2‐naphthyl)acryloyl) tropolones (5, 6, 7, 8). Compounds 1, 2, 3, 4 reacted with hydroxyamine to give 3‐[2‐(2‐naphthyl)vinyl]‐8__H__‐cyclohepta[d]isoxazol‐8‐ones (9, 10, 11, 12). The reactions of 1, 2, 3, 4 with phenylhydrazine and substituted phenylhydrazines gave 3‐[2‐(2‐naphthyl)vinyl]‐1‐phenylcyclohepta[c]pyrazol‐8(1__H__)‐ones (13, 14, 15, 16, 17, 18, 19, 20, 21). J. Heterocyclic Chem., (2009).