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Diazo compounds of the heterocyclic series. 6. Amination of methoxy-substituted 2-naphthyl- and 2-arylazobenzimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The amination of azo compounds inactivated by quaternization was carried out for the first time using 4-methoxyphenyl-, 2- and 4-methoxynaphthylazobenzimidazoles as examples. In contrast to the quaternary salts of 2-arylazobenzimidazoles, during the amination of the above bases of azo compounds, the substitution of the methoxy group rather than of the hydrogen atom was observed. The anomalous ease of substitution of the methoxy group, located in the naphthalene ring in a position adjacent to the azo bridge was attributed to the manifestation of an ortho-effect, discovered in the series of azo compounds for the first time.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, 344104, Rostov-on-Don

    S. N. Kolodyazhnaya, L. N. Divaeva, A. M. Simonov & N. N. Zheltikova

  2. S. M. Kirov Vitebsk State Pedagogical Institute, 210036, Vitebsk

    S. N. Kolodyazhnaya, L. N. Divaeva, A. M. Simonov & N. N. Zheltikova

Authors
  1. S. N. Kolodyazhnaya
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  2. L. N. Divaeva
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  3. A. M. Simonov
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  4. N. N. Zheltikova
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Additional information

For Communication 5, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1209–1214, September, 1991.

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Kolodyazhnaya, S.N., Divaeva, L.N., Simonov, A.M. et al. Diazo compounds of the heterocyclic series. 6. Amination of methoxy-substituted 2-naphthyl- and 2-arylazobenzimidazoles. Chem Heterocycl Compd 27, 970–975 (1991). https://doi.org/10.1007/BF00484360

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  • DOI: https://doi.org/10.1007/BF00484360

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