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Reduction of 4-arylazoindoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established that 4-acetamido-5-hydroxyindole derivatives are formed in the reduction of 4-phenylazo-5-hydroxyindole derivatives with zinc dust in acetic acid in the presence of acetic anhydride and sodium acetate. However, p-semidine rearrangement of the intermediate hydrazo derivatives is observed in the analogous reduction of 4-arylazo-5-methoxyindoles, and 4-acetamido-5-methoxy-7-arylaminoindoles are formed. The latter are oxidized by oxygen and nitric acid to 4-oxo-7-arylimino-4,7-dihydroindoles; nitration of the arylimino ring occurs in some cases under the influence of nitric acid.

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Literature cited

  1. V. I. Shvedov, G. N. Kurilo, A. A. Cherkasova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 8, 1096 (1975).

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119021, Moscow

    G. N. Kurilo, N. I. Rostova, A. A. Cherkasova, K. F. Turchin, L. M. Alekseeva & A. N. Grinev

Authors
  1. G. N. Kurilo
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  2. N. I. Rostova
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  3. A. A. Cherkasova
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  4. K. F. Turchin
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  5. L. M. Alekseeva
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  6. A. N. Grinev
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1374–1379, October, 1980.

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Kurilo, G.N., Rostova, N.I., Cherkasova, A.A. et al. Reduction of 4-arylazoindoles. Chem Heterocycl Compd 16, 1043–1048 (1980). https://doi.org/10.1007/BF00496607

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  • DOI: https://doi.org/10.1007/BF00496607

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