Abstract
The possibility of using certain ketimines in place of mixtures of ketone and amine in the synthesis of indoles from 3-nitropyridinium salts has been demonstrated. The use of ketimines leads, in many cases, to increased yields of indoles and simplifies their isolation. It has been established that the rate of indole formation is considerably increased in polar aprotic solvents.
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A. Z. Afanas'ev, M. A. Yurovskaya, and Yu. G. Bundel', Khim. Gererotsikl. Soedin., No. 1, 134 (1987).
S. P. Gromov and Yu. G. Bundel', Dokl. Akad. Nauk SSSR, 281, 585 (1985).
M. A. Yurovskaya, V. A. Chertkov, A. Z. Afanas'ev, F. V. Ienkina, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 4, 509 (1985).
M. A. Yurovskaya, M. Bkhaumik, and Yu. G. Bundel', Vestn. MGU, 26, 490 (1985).
R. W. Layer, Chem. Rev., 63, 489 (1963).
American Home Products Corp., British Patent 702,980 (1955); Chem. Abstr. 49, 5515 (1955).
H. G. Rajaharison and C. M. Roussel, European Patent 69,641; Chem. Abs., 101, 23334 (1984).
M. Bkhaumik, Dissertation, Moscow State University (1985), p. 95.
P. J. von Rijn, Rec. Trav. Cheim., 45, 267 (1926).
E. Profft and F. Melichan, J. Prakt. Chem., 274, 87 (1955).
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For Communication 3, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1625–1628, December, 1987.
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Yurovskaya, M.A., Afanas'ev, A.Z., Chertkov, V.A. et al. Synthesis of indoles from pyridinium salts. 4. Ketimines in the synthesis of indoles from 3-nitropyridinium salts. Chem Heterocycl Compd 23, 1305–1308 (1987). https://doi.org/10.1007/BF00472252
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DOI: https://doi.org/10.1007/BF00472252