A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

• 作者: Dingqiao Yang Xiongjun Zuo Xiuli Liang Yuhua Long
• 来源期刊: 有机化学国际期刊(英文)
• 学科: 化学
• 关键词: The Intramolecular Friedel-Crafts Acylation Reaction: 9 10-Dimethoxybenzo [6 7]oxepino[3 4-b]quinolin-13(6H)-one and Its DERIVATIVES 6 7-Dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic Acid: Ethyl 7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylate: PPA
• 年，卷（期）: yjhxgjqkyw,（2）
• 页码范围: 119-124
• 页数: 6页
• 分类号: O6

摘要

A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.