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Investigation of quinones

XXVII. Reaction of 2-arylanthraquinonetriazoles with amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The action of primary and secondary amines on 2-arylanthraquinonetriazoles results in substitution of the hydrogen atom in the 4 position to form 4-amino derivatives. The activity of 2-arylanthraquinonetriazoles in amination is less than that of the previously studied anthraquinone-1, 2,5-X-diazoles (X=O, S, Se). This is explained by the electron-donor effect of the aryl group in the 2 position and the lower degree of alternation of the bonds in the ring adjacent to the heteroring, which leads to a decrease in the effectiveness of transmission of the electron-acceptor effect to the reaction center in the 4 position.

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Authors and Affiliations

  1. Scientific-Research Institute of Organic Intermediates and Dyes, Moscow

    M. V. Gorelik & M. S. Kharash

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  1. M. V. Gorelik
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  2. M. S. Kharash
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See [1] for communication XXVI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1574–1580, November, 1971.

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Gorelik, M.V., Kharash, M.S. Investigation of quinones. Chem Heterocycl Compd 7, 1464–1470 (1971). https://doi.org/10.1007/BF00481121

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  • DOI: https://doi.org/10.1007/BF00481121

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