ChemInform Abstract: Efficient Preparation of Substituted 5,6,7,8-Tetrahydroquinolines and Octahydroacridine Derivatives.

✍ Scribed by Dirk Sielemann; Ralf Keuper; Nikolaus Risch

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199947163

✦ Synopsis

Efficient Preparation of Substituted 5,6,7,8-Tetrahydroquinolines and Octahydroacridine Derivatives.

-Enamine (II) reacts with β-amine ketone hydrochloride (I) to afford the diketones (III) in moderate to good yields. The final cyclization to tetrahydroquinolines (IV) is achieved by refluxing (III) in the presence of an ammonia source. However, the cyclization of (III) can be carried out without isolation of these intermediates, thus providing higher yields of (IV). In the reaction of Mannich bases (V) with (VI) the intermediate 1,5-diketone is cyclized in situ to give compounds (VII). This method is more simple and furnishes better than known literature methods. -(SIELEMANN,