Skip to main content
Log in

Intramolecular reactions in the oxindole series

  • Kurze Mitteilungen
  • Published:
Experientia Aims and scope Submit manuscript

Zusammenfassung

Es werden verschiedene Reaktionen in der Oxindolreihe diskutiert. Man kann sie sich als ähnliche Mechanismen vorstellen, da alle über intramolekular gebildete Zwischenprodukte bzw. Endprodukte laufen.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. R. Goutarel, M.-M. Janot, V. Prelog, andW. I. Taylor, Helv. chim. Acta33, 150 (1950).

    Article  CAS  Google Scholar 

  2. For the best review seeP. L. Julian, E. W. Meier, andH. C. Printy, inHeterocyclic Compounds, Vol. III (John Wiley & Sons, Inc., New York, 1952), Chapter 1, pp. 161 and 225.

    Google Scholar 

  3. P. L. Julian, H. C. Printy, R. Ketcham, andR. Doone, J. Amer. Chem. Soc.75, 5305 (1953).

    Article  CAS  Google Scholar 

  4. It is interesting to note that the cyclization of compounds containing two hetero atoms results in the formation of 5-membered lactams; e.g.: [P. W. Neber, Ber. dtsch. chem. Ges.55, 826 (1922).

    Article  Google Scholar 

  5. P. W. Neber andH. Keppler, Ber. dtsch. chem. Ges.57, 778 (1924).

    Article  Google Scholar 

  6. J. Martinet andO. Dornier, C. r. Acad. Sci.172, 1415 (1921).

    CAS  Google Scholar 

  7. F. J. Di Carlo, J. Amer. Chem. Soc.66, 1420 (1944)].

    Article  Google Scholar 

  8. P. L. Julian, E. W. Meier, andH. C. Printy, Note 1, p. 418.

  9. P. L. Julian, E. W. Meier, andH. C. Printy inHeterocyclic Compounds, Vol. III (John Wiley & Sons, Inc., New York, 1952), Chapter 1.

    Google Scholar 

  10. R. B. Woodward andR. H. Eastman, J. Amer. Chem. Soc.72, 399 (1950).

    Article  CAS  Google Scholar 

  11. P. L. Julian, H. C. Printy, R. Ketcham, andR. Doone, J. Amer. Chem. Soc.75, 5305 (1953).

    Article  CAS  Google Scholar 

  12. B. Witkop, J. Amer. Chem. Soc.72, 2311 (1950).

    Article  CAS  Google Scholar 

  13. T. Hoshino et al., Ann. Chem.500, 42 (1932);520, 19 (1935).

    Article  CAS  Google Scholar 

  14. P. L. Julian andJ. Pikl, J. Amer. Chem. Soc.57, 539 (1935).

    Article  CAS  Google Scholar 

  15. R. B. Woodward andE. Wenkert, unpublished results. The authors express their thanks to ProfessorWoodward for permission to include the above data in this article.

  16. As a sidelight to the above discussion, the interesting thermal rearrangement of 3-acylindole hydrazones should be noted [C. Alberti, Gazz. Chim. ital.77, 398 (1947)]. This reaction may be postulated to proceed via an internally interacted intermediate which breaks up into the more thermodynamically stable aminophenylpyrazole:

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wenkert, E., Reid, T.L. Intramolecular reactions in the oxindole series. Experientia 10, 417–418 (1954). https://doi.org/10.1007/BF02318503

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02318503

Keywords

Navigation