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Name Reactions pp 263-265 | Cite as

Gould–Jacobs reaction

  • Jie Jack Li
Chapter

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.

Keywords

Inorganic Chemistry Organic Chemistry Medical Research Pyridine Ring Heterocyclic Chemistry 
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.

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References

  1. 1.
    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.Google Scholar
  2. 2.
    Reitsema, R. H. Chem. Rev. 1948, 53, 43–68. (Review).Google Scholar
  3. 3.
    Cruickshank, P. A., Lee, F. T., Lupichuk, A. J. Med. Chem. 1970, 13, 1110–1114.CrossRefGoogle Scholar
  4. 4.
    Elguero J., Marzin C., Katritzky A. R., Linda P., The Tautomerism of Heterocycles, Academic Press, New York, 1976, pp 87–102. (Review).Google Scholar
  5. 5.
    Wang, C. G., Langer, T., Kiamath, P. G., Gu, Z. Q., Skolnick, P., Fryer, R. I. J. Med. Chem. 1995, 38, 950–957.CrossRefGoogle Scholar
  6. 6.
    Milata, V.; Claramunt, R. M.; Elguero, J.; Zálupský, P. Targets in Heterocyclic Systems 2000, 4, 167–203. (Review).Google Scholar
  7. 7.
    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).Google Scholar
  8. 8.
    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.CrossRefGoogle Scholar
  9. 9.
    Desai, N. D. J. Heterocycl. Chem. 2006, 43, 1343–1348.CrossRefGoogle Scholar
  10. 10.
    Kendre, D. B.; Toche, R. B.; Jachak, M. N. J. Heterocycl. Chem. 2008, 45, 1281–1286.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  1. 1.Dept. Discovery ChemistryBristol-Myers Squibb CompanyWallingfordUSA

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