A novel access to 2,4-substituted quinolines from acetylenic ketones

✍ Scribed by T. Masquelin; D. Obrecht

• Book ID: 104207406
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 408 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01025-3

✦ Synopsis

2, 4-Substituted quinolines of type 7 and 8 were synthesized starting from 2-amino thiophenol and acetylenic acetals 5 to yield various substituted benzo[b][l, 41 thiazepine intermediates of type 6. Subsequent sulfur extrusion in refluxing toluene led to 2, 4-substituted quinoline acetals 7, which were transformed into the corresponding 2-substituted quinoline-4carbaldehydes 8 in good to excellent yields.