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

Author(s): Dingqiao Yang | Xiuli Liang | Xiongjun Zuo | Yuhua Long

Journal: International Journal of Organic Chemistry
ISSN 2161-4687

Volume: 03;
Issue: 02;
Start page: 119;
Date: 2013;
Original page

Keywords: 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; 6 | 7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylate: PPA

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.
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