Gould–Jacobs reaction
The Gould–Jacobs reaction is an organic synthesis for the preparation of quinolines (more specifically, a 4-quinolinol).[1] In this reaction aniline or an aniline derivative first reacts with malonic acid derivative ethyl ethoxymethylenemalonate with substitution of the ethoxy group by nitrogen. A benzannulation takes place by application of heat to a quinoline. The ester group is hydrolysed by sodium hydroxide to the carboxylic acid and decarboxylation again by application of heat to 4-hydroxyquinoline.
Examples
An example is the synthesis of 4,7-dichloroquinoline [5]
- Floctafenine and Glafenine are a pair of fenamate NSAIDs whose synthesis rely on the Gould–Jacobs reaction.
- A lot of quinolone antibiotic structures such as Rosoxacin, Oxolinic acid, Droxacin, etc.
References
- ↑ Gould, R. Gordon; Jacobs, Walter A. (1939). "The Synthesis of Certain Substituted Quinolines and 5,6-Benzoquinolines". J. Am. Chem. Soc. 61 (10): 2890–2895. doi:10.1021/ja01265a088.
- ↑ Li, Jie Jack (2009). "Gould–Jacobs reaction". Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications (4th ed.). Springer-Verlag. pp. 263–265. ISBN 9783642010538. doi:10.1007/978-3-642-01053-8_113.
- ↑ Lengyel, László Csaba; Sipos, Gellért; Sipőcz, Tamás; Vágó, Teréz; Dormán, György; Gerencsér, János; Makara, Gergely; Darvas, Ferenc (2015). "Synthesis of Condensed Heterocycles by the Gould–Jacobs Reaction in a Novel Three-Mode Pyrolysis Reactor". Org. Process Res. Dev. 19 (3): 399–409. doi:10.1021/op500354z.
- ↑ "Gould–Jacobs Reaction". Comprehensive Organic Name Reactions and Reagents. 276: 1252–1255. 2010. doi:10.1002/9780470638859.conrr276.
- ↑ Price, Charles C.; Roberts, Royston M. (1948). "4,7-Dichloroquinoline (Quinoline, 4,7-dichloro-)". Org. Synth. 28: 38. doi:10.15227/orgsyn.028.0038.; Coll. Vol., 3, p. 272
This article is issued from
Wikipedia.
The text is licensed under Creative Commons - Attribution - Sharealike.
Additional terms may apply for the media files.