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Molecules 2013, 18(3), 3227-3240; doi:10.3390/molecules18033227
Article

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

* ,
,
 and
Biomedical Research Centre, Sheffield Hallam University, Howard Street, Sheffield, S1 1WB, UK
* Author to whom correspondence should be addressed.
Received: 30 January 2013 / Revised: 1 March 2013 / Accepted: 4 March 2013 / Published: 13 March 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

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.
Keywords: synthesis; 4-quinolylpropionic esters; Gould-Jacobs reaction; anti-microbial activity synthesis; 4-quinolylpropionic esters; Gould-Jacobs reaction; anti-microbial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Khan, M.A.; Miller, K.; Rainsford, K.D.; Zhou, Y. Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates. Molecules 2013, 18, 3227-3240.

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