Synthesis of <i>N</i>-Benzyl-3-anilinopropanamides and Cyclization to 4-Hydroxy-4-<i>N</i>-benzylamino-1,2,3,4-tetrahydroquinoline

• 作者: Chukwuemeka A. Nwadinigwe Lami A. Nnamonu Vincent C. Agwada
• 来源期刊: 有机化学国际期刊(英文)
• 学科: 化学
• 关键词: 3-Anilinopropanamide N-Benzylanilinopropanamide 1 2 3 4-Tetrahydroquinoline
• 年，卷（期）: 2013,（4）
• 页码范围: 229-234
• 页数: 6页
• 分类号: O6

摘要

Substituted 3-anilinopropanamides were converted to N-benzyl derivatives via uncatalyzed amine exchange reaction with benzylamine in up to 41% yield. Unprotected aniline nitrogen had been observed to inhibit facile cyclization. An attempt was therefore made to protect the N by acetylation prior to cyclization. During this process, facile ring closure occurred in the methoxy series to give 4-hydroxy-4-N-benzylamino-1,2,3,4-tetrahydroquinolines in up to 69% yield.