Gould-Jacobs reaction
The Gould-Jacobs reaction is a name reaction in organic chemistry that was named after its discoverers Gordon Gould (1920–2005) and Walter Abraham Jacobs (1883–1967). It is used for the production of quinoline derivatives .
Overview reaction
4-Hydroxyquinolines are produced from aniline (or aniline derivatives) by reaction with alkoxymethylene malonic acid esters in a cascade of reactions.
mechanism
The aniline derivative substituted, the alkoxy group nucleophilically at the electron- deficient C = C double bond of the Methylidenmalonsäureesters to a anilinomethylene-malonic acid dialkyl ester, in a similar Friedel-Crafts reaction to a quinoline fused . This is hydrolyzed to a quinoline carboxylic acid . The tautomeric β-keto ester decarboxylates to 4-hydroxyquinoline.
One application example is the synthesis of 4,7-dichloroquinoline.
Individual evidence
- ^ R. Gordon Gould, Walter Abraham Jacobs : The Synthesis of Certain Substituted Quinolines and 5,6-Benzoquinolines . In: J. Am. Chem. Soc. 61, No. 10, 1939, pp. 2890-2895, doi: 10.1021 / ja01265a088 .
- ^ Jie Jack Li: Name Reactions: A Collection of Detailed Reaction Mechanisms . 3rd exp. ed., Springer, Berlin 2006, ISBN 978-3-540-30030-4 , p. 269 ( Google Books ).
- ^ Charles C. Price and Royston M. Roberts: 4,7-Dichloroquinoline In: Organic Syntheses . 28, 1948, p. 38, doi : 10.15227 / orgsyn.028.0038 ; Coll. Vol. 3, 1955, p. 272 ( PDF ).
