Gould-Jacobs quinoline synthesis

What is Gould-Jacobs quinoline synthesis?

In 1939, Gould and Jacobs reported the synthesis of 4-hydroxyquinolines from anilines and diethyl ethoxymethylenemalonate (DEEMM), which involves the condensation to anilinomethylenemalonate, cyclo-acylation to quinolin-4-one nucleus, and subsequent hydrolysis and decarboxylation.

Gould-Jacobs quinoline synthesis - general reaction scheme - Gould-Jacobs reaction
Gould-Jacobs quinoline synthesis

Gould-Jacobs quinoline synthesis is commonly known as the Gould-Jacobs reaction and is useful for synthesizing piperazine and pyrrolidine analogues, particularly with electron-donating groups at the meta-position of the aniline substrate.

References

The Synthesis of Certain Substituted Quinolines and 5,6-Benzoquinolines
R. Gordon. Gould and Walter A. Jacobs
Journal of the American Chemical Society 1939 61 (10), 2890-2895
DOI: 10.1021/ja01265a088

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