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.
References
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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).
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R. B. Woodward andE. Wenkert, unpublished results. The authors express their thanks to ProfessorWoodward for permission to include the above data in this article.
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:
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Wenkert, E., Reid, T.L. Intramolecular reactions in the oxindole series. Experientia 10, 417–418 (1954). https://doi.org/10.1007/BF02318503
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DOI: https://doi.org/10.1007/BF02318503