Abstract
3-Indolylalkanoic acids (III) were obtained from 3-acylindoles (I) under the conditions of the Willgerodt-Kindler reaction. The reactivity of I falls as the chain lengthens and 3-caproylindole does not undergo reaction. Removal of the carbonyl group away from the indole ring promotes the conversion of the ketones to III. Sulfur-containing compounds, the structure of which was studied, were isolated along with the intermediate products — thiomorpholides of indolylalkanoic acids (II).
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V. Kayumov, Yu. I. Smushkevich, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 756 (1973).
Yu. A. Baskakov and N. N. Mel'nikov, Collection of Papers on General Chemistry [in Russian], Vol. 1, Izd. Akad. Nauk SSSR, Moscow (1953), p. 712.
Yu. A. Baskakov and N. N. Mel'nikov, Physiology of Plants [in Russian], Vol. 3, Izd. Akad. Nauk SSSR, Moscow (1956), p. 208.
G. Buchmann and D. Rossner, J. Prakt. Chem., 25, 117 (1964).
P. Stefanescu, Rev. China., 20, 65 (1969).
F. P. Doyle, W. Ferrier, D. O. Holland, and M. D. Menta, J. Chem. Soc., 2853 (1956).
J. E. Saxton, J. Chem. Soc., 3592 (1952).
B. Oddo and Z. Sessa, Gazz. Chim. Ital., 41, No. 1, 234 (1911).
D. O. Holland and J. H. C. Nayler, J. Chem. Soc., 280 (1953).
H. E. Fritz, U. S. Patent No. 3,051,723 (1962); Chem. Abstr., 57, 13,727 (1962); J. Org. Chem., 28, 1384 (1963).
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See [1] for communication LXXXIV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 759–761, June, 1973.
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Avramenko, V.G., Shirnyuk, T.Y. & Suvorov, N.N. Indole derivatives. Chem Heterocycl Compd 9, 698–700 (1973). https://doi.org/10.1007/BF00472310
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DOI: https://doi.org/10.1007/BF00472310