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

Dingqiao Yang, Xiuli Liang, Xiongjun Zuo, Yuhua Long

Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China.

DOI: 10.4236/ijoc.2013.32013                

Abstract

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.

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

Conflicts of Interest

The authors declare no conflicts of interest.

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