The Gould–Jacobs reaction is a sequence of the following reactions: a. Substitution of an aniline with either alkoxy methylenemalonic ester or acyl malonic ester providing the anilinomethylenemalonic ester; b. Cyclization of to the 4-hydroxy-3-carboalkoxyquinoline (4-hydroxyquinolines exist predominantly in 4-oxoform); c. Saponification to form acid; d. Decarboxylation to give the 4-hydroxyquinoline. Extension could lead to unsubstituted parent heterocycles with fused pyridine ring of Skraup type.
Access provided by Autonomous University of Puebla. Download to read the full chapter text
Chapter PDF
Similar content being viewed by others
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
References
Gould, R. G.; Jacobs, W. A. J. Am. Chem. Soc. 1939, 61, 2890–2895. R. Gordon Gould was born in Chicago in 1909. He earned his Ph.D. at Harvard University in 1933. After serving as an instructor at Harvard and Iowa, Gould worked at Rockefeller Institute for Medical Research where he discovered the Gould–Jacobs reaction with his colleague Walter A. Jacobs.
Reitsema, R. H. Chem. Rev. 1948, 53, 43–68. (Review).
Cruickshank, P. A., Lee, F. T., Lupichuk, A. J. Med. Chem. 1970, 13, 1110–1114.
Elguero J., Marzin C., Katritzky A. R., Linda P., The Tautomerism of Heterocycles, Academic Press, New York, 1976, pp 87–102. (Review).
Wang, C. G., Langer, T., Kiamath, P. G., Gu, Z. Q., Skolnick, P., Fryer, R. I. J. Med. Chem. 1995, 38, 950–957.
Milata, V.; Claramunt, R. M.; Elguero, J.; Zálupský, P. Targets in Heterocyclic Systems 2000, 4, 167–203. (Review).
Curran, T. T. Gould–Jacobs Reaction. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Corey, E. J., Eds.; Wiley & Sons: Hoboken, NJ, 2005, 423–436. (Review).
Ferlin, M. G.; Chiarelotto, G.; Dall’Acqua, S.; Maciocco, E.; Mascia, M. P.; Pisu, M. G.; Biggio, G. Bioorg. Med. Chem. 2005, 13, S3531–3541.
Desai, N. D. J. Heterocycl. Chem. 2006, 43, 1343–1348.
Kendre, D. B.; Toche, R. B.; Jachak, M. N. J. Heterocycl. Chem. 2008, 45, 1281–1286.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2009 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Li, J.J. (2009). Gould–Jacobs reaction. In: Name Reactions. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-01053-8_113
Download citation
DOI: https://doi.org/10.1007/978-3-642-01053-8_113
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-01052-1
Online ISBN: 978-3-642-01053-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)