Issue 25, 2016

Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity

Abstract

A novel method for the preparation of 2-carboxyl-3-aryl quinoline derivatives from anilines, ethyl glyoxalate and enol ethers as phenylacetaldehyde surrogates is reported. The three-component coupling reaction occurs rapidly under mild conditions in dichloromethane catalysed by TFA. The method allows a more direct access to 3-aryl quinolines, sidestepping issues encountered with phenylacetaldehyde derivatives. This chemistry was used to prepare quinolines with 3-diarylether functionality that showed low micromolar efficacy (IC50 range: 5–26 μM) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD50 ≥ 320 μM) towards the host cells.

Graphical abstract: Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity

Supplementary files

Article information

Article type
Communication
Submitted
17 May 2016
Accepted
26 May 2016
First published
26 May 2016

Org. Biomol. Chem., 2016,14, 5951-5955

Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity

C. E. Brown, J. McNulty, C. Bordón, R. Yolken and L. Jones-Brando, Org. Biomol. Chem., 2016, 14, 5951 DOI: 10.1039/C6OB01083K

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