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Indoles

XXVI. Ratio of indole isomers formed during the fischer cyclization of meta-substituted diethyl ketone phenylhydrazones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

cyclization of m-RC6H4NHN=C (C2H5)2 (R = C2H5, OCH3, Cl) under various conditions always gives a mixture of 4-R-3-methyl-2-ethylindole and 6-R-3-methyl-2-ethylindole isomers with predominance of the latter. The ratios of the isomers formed depend on the catalyst used.

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Literature cited

  1. I. I. Grandberg and S. B. Nikitina, Khim. Geterotsikl. Soedin., 1201 (1971).

  2. I. I. Grandberg, L. D. Belyaeva, and L. B. Dmitriev, Khim. Geterotsikl. Soedin., 58 (1971).

  3. B. Robinson, Chem. Rev., 63, 373 (1963).

    Google Scholar 

  4. N. N. Suvorov and N. P. Sorokina, Dokl. Akad. Nauk SSSR, 136, 840 (1961).

    Google Scholar 

  5. J. Szmuskovicz, E. M. Cleen, K. V. Heinzelman, J. B. Hester, and G. A. Youngdale, J. Med. Chem., 9, 527 (1966).

    Google Scholar 

  6. R. C. Elderfield, J. M. Lagowski, O. L. McCurdy, and S. L. Wythe, J. Org. Chem., 23, 435 (1958).

    Google Scholar 

  7. J. B. McKay, R. M. Parkhurst, R. M. Silverstein, and W. A. Skinner, Can. J. Chem., 41, 2585 (1963).

    Google Scholar 

  8. J. R. Piper and F. J. Stevens, J. Heterocycl. Chem., 3, 95 (1966).

    Google Scholar 

  9. N. N. Suvorov, Doctoral Dissertation [in Russian], Moscow (1962).

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See [1] for communication XXV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1204–1208, September, 1971.

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Grandberg, I.I., Belyaeva, L.D. & Dmitriev, L.B. Indoles. Chem Heterocycl Compd 7, 1131–1134 (1971). https://doi.org/10.1007/BF00510019

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  • DOI: https://doi.org/10.1007/BF00510019

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