Abstract
The reaction of the 1,2-diaryl-4-oxo-4,5,6,7-tetrahydroindoles, and 3-methyl-4-oxo-4,5,6,7-tetrahydroindole with tetracyanoethylene occurred at the 5 position of the tetrahydroindole ring. A Fischer rearrangement of the phenylhydrazones of these 4-oxotetrahydroindoles gave pyrrolo [2,3-c]carbazoles.
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Literature cited
R. I. Sunberg, The Chemistry of Indoles, Academic Press, New York (1970), p. 488.
W. E. Noland, W. C. Kuryla, and R. F. Lange, J. Am. Chem Soc., 81, 6010 (1959).
Y. Shirota, S. Ezaki, S. Kusabayashi, and H. Mikawa, Bull Chem. Soc. Japan, 45, 836 (1972).
A. P. Terent'ev and A. N. Kost, Reactions and Methods of Studying Organic Compounds [in Russian], 2nd Edn., GNTI Chemical Literature, Moscow-Leningrad (1952), p. 47.
O. E. Nasakin, V. A. Kukhtin, G. I. Petrov, E. G. Nikolaev, V. V. Alekseev, and S. Yu. Sil'vestrova, USSR Inventor's Cert. No. 759607; Byull. Izobr., No. 38, 38 (1980).
W. J. Middleton, R. E. Heckert, E. Z. Little, and C. G. Krespan, J. Am. Chem. Soc., 80, 2783 (1958).
O. E. Nasakin, V. V. Alekseev, P. B. Terent'ev, A. Kh. Bulai, and V. A. Shmorgunov, Khim. Geterotsikl. Soedin., No. 12, 1605 (1982).
K. Dagher, P. B. Terent'ev (Terentiev), Yu. G. Bundel, R. Hanna, and B. I. Maximov, J. Heterocycl. Chem., 20, 989 (1983).
K. Dagher and P. B. Terent'ev, Khim. Geterotsikl. Soedin., 12, 1462 (1984).
K. Dagher and P. B. Terent'ev (Terentiev), A. N. Kost, Yu. G. Bundel, B. I. Maximov, and R. Hanna, J. Heterocycl. Chem., 19, 645 (1982).
R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1984).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 217–221, February, 1986.
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Dagher, K., Terent'ev, P.B. & Kulikov, N.S. Tetracyanoethylation and fischer rearrangement of some 4-oxo-4,5,6,7-tetrahydroindoles. Chem Heterocycl Compd 22, 172–175 (1986). https://doi.org/10.1007/BF00519938
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DOI: https://doi.org/10.1007/BF00519938