Abstract
It was established that indole and 2-methylindole are converted in soil to stable compounds, which were isolated and identified by means of mass spectrometry (low-and high-resolution), IR, UV, and PMR spectroscopy, and by comparison with model samples. Under the influence of peroxide compounds in the soil, indole is converted to 2,2-di(3-indolyl)indoxyl and very small amounts of indoxylrot, indirubin, and indigo. Similarly, 2-methylindole is converted in soil to 2-methyl-2-(2-methyl-3-indolyl)-3-oxoindoline.
Similar content being viewed by others
Literature cited
V. A. Medvedev, G. P. Lipnitskaya, A. K. Sheinkman, and V. D. Davydov, Pochvovedenie, No. 3, 32 (1975).
V. A. Medvedev and V. D. Davydov, Pochvovedenie, No. 11, 57 (1972).
A. R. Katritzky, Rec. Trav. Chim., 78, 995 (1959).
A. Stern and K. Timmons, Electron Absorption Spectroscopy in Organic Chemistry [Russian translation], Mir, Moscow (1974), p. 202.
O. Schmitz-DuMont, K. Hamann, and K. H. Geller, Ann., 504, 1 (1933).
B. Witkop, J. Patrik, and H. Kissmann, Ber., 85, 949 (1952).
A. G. Holmes-Siedle and B. Sannders, Chem. and Ind., No. 3, 265 (1957).
S. H. Loo and D. O. Woolf, Chem. Ind., No. 9, 1123 (1957).
I. C. Powers, J. Org. Chem., 90, 678 (1968).
R. Marchelli, W. D. Jamieson, S. Safe, O. Hutzinger, and R. A. Heacock, Can. J. Chem., 49, 1296 (1971).
R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).
G. I. Zhungietu and L. P. Sinyavskaya, Khim. Geterotsikl. Soedin., No. 2, 204 (1976).
I. M. Rice, G. O. Dudek, and M. Barber, J. Am. Chem. Soc., 89, 4569 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1490–1496, November, 1978.
Rights and permissions
About this article
Cite this article
Sheinkman, A.K., Klyuev, N.A., Rybenko, L.A. et al. Transformation of indole in soil. Chem Heterocycl Compd 14, 1211–1216 (1978). https://doi.org/10.1007/BF00509739
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00509739