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Synthesis and keto-enol tautomerism of ethyl 4-oxo-3,4-dihydro-1H-pyrano[3,4-b]quinoline-3-carboxylate

  • Ming-Qin Chang EMAIL logo , Feng Gao , Yang Li and Wen-Tao Gao
Published/Copyright: January 9, 2013
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Chemical Papers
From the journal Chemical Papers Volume 67 Issue 4

Abstract

An efficient method has been developed for the synthesis of a novel β-keto ester-containing pyranoquinoline compound, i.e., ethyl 4-oxo-3,4-dihydro-1H-pyrano[3,4-b]quinoline-3-carboxylate. The method entails a two-step synthesis. The first step involves the Williamson-type reaction of ethyl 2-bromomethyl-3-quinoline-3-carboxylate with ethyl hydroxyacetate in anhydrous benzene to afford the intermediate ethyl 2-[(2-ethoxy-2-oxoethoxy)methyl]quinoline-3-carboxylate. The second step includes the Dieckmann condensation reaction of the resulting intermediate in the presence of sodium ethoxide in anhydrous toluene to afford the desired pyranoquinoline containing β-keto ester moiety. Keto-enol tautomerism of the compound thus obtained was investigated by spectroscopic methods.

Keywords: pyranoquinoline; β-keto ester; Williamson-type reaction; ethyl hydroxyacetate; Dieckmann condensation; keto-enol tautomerism

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Published Online: 2013-1-9
Published in Print: 2013-4-1

© 2012 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.2478/s11696-012-0276-6
Keywords for this article
pyranoquinoline; β-keto ester; Williamson-type reaction; ethyl hydroxyacetate; Dieckmann condensation; keto-enol tautomerism

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