Synthesis and Cyclization of 8-Formyl-2-（phenoxymethyl）- quinoline-3-carboxylic Acids

A facile synthesis of a series of new quinoline-8-carbaldehyde compounds, namely 8-formyl-2- （phenoxymethyl）quinoline-3-carboxylic acids （4a--4h） and 13-oxo-6,13-dihydro[1]benzoxepino[3,4-b]quinoline- 8-carbaldehyde （5a--5g） is described, involving the one-pot synthesis reaction of ethyl 2-（chlorome...

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Published in中国化学：英文版 Vol. 30; no. 5; pp. 1127 - 1132
Main Author 高文涛 赵治刚 李阳 闫岩 李凤
Format Journal Article
LanguageEnglish
Published 2012
Subjects
分子内环化反应
合成反应
喹啉
多聚磷酸
氧
简便合成
羧酸
苯
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ISSN1001-604X
1614-7065

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Summary:A facile synthesis of a series of new quinoline-8-carbaldehyde compounds, namely 8-formyl-2- （phenoxymethyl）quinoline-3-carboxylic acids （4a--4h） and 13-oxo-6,13-dihydro[1]benzoxepino[3,4-b]quinoline- 8-carbaldehyde （5a--5g） is described, involving the one-pot synthesis reaction of ethyl 2-（chloromethyl）-8- formylquinoline-3-carboxylate （3） with substituted phenols followed by the intramolecular cyclization reaction via the treatment with polyphosphoric acid （PPA）. Quinoline-8-carbaldehydes 4a--4h and 5a--5g are novel and their structures were supported by IR, IH NMR, 13C NMR, MS and elemental analysis.
Bibliography:A facile synthesis of a series of new quinoline-8-carbaldehyde compounds, namely 8-formyl-2- （phenoxymethyl）quinoline-3-carboxylic acids （4a--4h） and 13-oxo-6,13-dihydro[1]benzoxepino[3,4-b]quinoline- 8-carbaldehyde （5a--5g） is described, involving the one-pot synthesis reaction of ethyl 2-（chloromethyl）-8- formylquinoline-3-carboxylate （3） with substituted phenols followed by the intramolecular cyclization reaction via the treatment with polyphosphoric acid （PPA）. Quinoline-8-carbaldehydes 4a--4h and 5a--5g are novel and their structures were supported by IR, IH NMR, 13C NMR, MS and elemental analysis.
31-1547/O6
Gao Wentao, Zhao Zhigang,Li Yang, Yan Yan, Li Feng（Institute of Superfine Chemicals, Bohai University, Jinzhou, Liaoning 121000, China）
benzoxepinoquinoline, quinoline-8-carbaldehyde, one-pot, polyphosphoric acid （PPA）, cyclization reaction
ISSN:1001-604X
1614-7065