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Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates

Author(s): M. Akram Khan | Keith Miller | Kim Drummond Rainsford | Yong Zhou

Journal: Molecules
ISSN 1420-3049

Volume: 18;
Issue: 3;
Start page: 3227;
Date: 2013;
Original page

Keywords: synthesis | 4-quinolylpropionic esters | Gould-Jacobs reaction | anti-microbial activity

Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylene)malonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to form 4-chloroquinolines, which reacted on heating with diethyl sodiomethylmalonate in DMF to yield moderate yields of substituted ethyl 2-(quinolin-4-yl)propanoates, many of which showed potent antimicrobial activity against Helicobacter pylori.
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