Abstract
The cyclization of diethyl ketone m-nitrophenylhydrazone under different conditions always gives a mixture of the isomeric 4-nitro-3-methyl-2-ethylindole and 6-nitro-3-methyl-2-ethylindole, generally with a certain predominance of the former. The isomer ratio depends on the nature of the catalyst used. Only 6-nitro-2,3,3-trimethylindolenine is formed in the cyclization of methyl isopropyl ketone m-nitrophenylhydrazone.
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I. I. Grandberg and V. I. Sorokin, Khim. Geterotsikl. Soedin., 31 (1973).
I. I. Grandberg, L. D. Belyaeva, and L. B. Dmitriev, Khim. Geterotsikl. Soedin., 58 (1971).
I. I. Grandberg, L. D. Belyaeva, and L. B. Dmitriev, Khim. Geterotsikl. Soedin., 1204 (1971).
I. I. Grandberg, L. D. Belyaeva, and L. B. Dmitriev, Dokl. Moskovsk. Sel'skokhoz. Akad. im. Timiryazeva, No. 162, 398 (1971).
R. B. Van Order and H. G. Lindwall, Chem. Rev., 30, 78 (1942).
K. Schofield and P. S. Theobald, J. Chem. Soc., 796 (1949).
C. Atkinson, J. Simpson, and A. Taylor, J. Chem. Soc., 167 (1954).
W. Borshe, A. Witte, and W. Bothe, Ann., 359, 49 (1908).
S. G. P. Plant, J. Chem. Soc., 2493 (1929).
S. G. P. Plant and D. W. Whitaker, J. Chem. Soc., 283 (1940).
S. G. P. Plant, J. Chem. Soc., 899 (1936).
J. B. McKay, R. M. Parkhurst, R. M. Silverstein, and W. A. Skinner, Can. J. Chem., 41, 2585 (1963).
G. M. Robinson and R. Robinson, J. Chem. Soc., 125, 827 (1924).
C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press (1969).
R. S. Kapil and S. S. Joshi, J. Indian Chem. Soc., 36, 417 (1959).
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See [1] for communication XXXIV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 37–39, January, 1973.
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Grandberg, I.I., Belyaeva, L.D. & Dmitriev, L.B. Indoles. Chem Heterocycl Compd 9, 31–33 (1973). https://doi.org/10.1007/BF00476143
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DOI: https://doi.org/10.1007/BF00476143