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Synthesis and structure of nitro-substituted 6(5H)-phenanthridinones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the preparation of nitro-substituted 6(5h)-phenanthridinones were examined. The nitration of 6(5H)-phenanthridinone, 5-methyl-6-(5H)- phenanthridinone, and 2-bromo-6(5H)-phenanthridinone was studied, and 2-, 3-, 4-nitro-, 2,4-, 2,8-, 4,8-dinitro-, 2,4,8-trinitro-, and 2,4,8,10-tetranitro-6(5H)-phenanthridinones, 2,4,8-trinitro- and 2,4,8,10-tetranitro-6-(5H)-phenanthridinones, and 2-bromo-4,8-dinitro- and 2-bromo-4,8,10-trinitro-6-(5H)-phenanthridinones were obtained. Proton magnetic resonance spectroscopy was used to identify the structure and predict the orientation of substitution in the nitration of 6(5H)-phenanthridinone and its nitro-substituted derivatives. The distribution of the electron density in these compounds was evaluated from an analysis of the chemical shifts of the protons.

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Authors and Affiliations

  1. Scientific-Research Institute of Organic Intermediates and Dyes, 103787, Moscow

    A. M. Andrievskii, A. N. Poplavskii, K. M. Dyumaev, Yu. S. Bogachev & S. S. Berestova

  2. L. Ya. Karpov Scientific-Research Institute of Physical Chemistry, 107120, Moscow

    A. M. Andrievskii, A. N. Poplavskii, K. M. Dyumaev, Yu. S. Bogachev & S. S. Berestova

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  1. A. M. Andrievskii
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  2. A. N. Poplavskii
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  3. K. M. Dyumaev
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  4. Yu. S. Bogachev
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  5. S. S. Berestova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1106–1113, August, 1985.

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Andrievskii, A.M., Poplavskii, A.N., Dyumaev, K.M. et al. Synthesis and structure of nitro-substituted 6(5H)-phenanthridinones. Chem Heterocycl Compd 21, 924–931 (1985). https://doi.org/10.1007/BF00519824

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  • DOI: https://doi.org/10.1007/BF00519824

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