Abstract
Under the influence of phosphorus oxychloride in an inert solvent, 1-aryl-2-acylhydrazines undergo intramolecular rearrangement to give 2-amino-3-alkylindoles. The latter are autooxidized in alkaline media to give 3-hydroxy-2-aminoindolenines or 3-hydroxy-2-iminoindolines. The structures of all of the compounds were proved by UV, IR, and PMR spectroscopy and also by mass-spectrometric data.
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L, G. Yudin, A. N. Kost, and E. Ya. Zinchenko, Khim. Geterotsikl. Soedin., 332 (1973).
Yu. N. Portnov, G. A. Golubeva, and A. N. Kost, Khim. Geterotsikl. Soedin., 61 (1972).
R. S. Sagitullin, V. I. Gorbunov, A. N. Kost, N.B. Kuplet-skaya, and V. V. Chistyakov, Khim. Geterotsikl. Soedin., 364 (1970).
W. E. Stewart and T. H. Siddall, Chem. Rev., 70, 517 (1970).
A. N. Kost, G. A. Golubeva, and Yu. N. Portnov, Dokl. Akad. Nauk SSSR, 200, 342 (1970).
L. G. Yudin, V. A. Budylin, A. N. Kost, and V. I. Minkin, Dokl. Akad. Nauk SSSR, 176, 1096 (1967).
M. Nakagawa, H. Tamaguchi, and T. Hino, Tetrahedron Lett., 4035 (1970).
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See [1] for communication XXXIV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 511–515, April, 1973.
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Golubeva, G.A., Portnov, Y.N. & Kost, A.N. Chemistry of indole. Chem Heterocycl Compd 9, 471–475 (1973). https://doi.org/10.1007/BF00471528
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DOI: https://doi.org/10.1007/BF00471528