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Synthesis and structure of bromonitro-6(5H)-phenanthridinones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Treatment of 2-bromo-6(5H)-phenanthridone with nitrating mixture or fuming nitric acid results in nitration, debromination, and bromination in the 10-position. The brominating agent is apparently Br+, formed in the reaction mixture following replacement of the bromine in the 2-position by a nitro-group. Monocrystals of 2-bromo-1,4,8-trinitro-6(5H)-phenanthridinone and 10-bromo-2,4,8-trinitro-6(5H)-phenanthridinone have been subjected to x-ray diffraction examination. PMR has been used for structural identification.

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Authors and Affiliations

  1. Research Institute for Organic Intermediates and Dyes, 103787, Moscow

    A. M. Andrievskii, O. V. Chelysheva, A. N. Poplavskii, V. V. Nikonov, L. A. Chetkina, V. K. Bel'skii, V. E. Zavodnik, A. A. Perov, N. A. Andronova & K. M. Dyumaev

  2. L. Ya. Karpov Research Institute for Physical Chemistry, 103064, Moscow

    A. M. Andrievskii, O. V. Chelysheva, A. N. Poplavskii, V. V. Nikonov, L. A. Chetkina, V. K. Bel'skii, V. E. Zavodnik, A. A. Perov, N. A. Andronova & K. M. Dyumaev

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  1. A. M. Andrievskii
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  2. O. V. Chelysheva
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  3. A. N. Poplavskii
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  4. V. V. Nikonov
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  5. L. A. Chetkina
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  6. V. K. Bel'skii
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  7. V. E. Zavodnik
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  8. A. A. Perov
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  9. N. A. Andronova
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  10. K. M. Dyumaev
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 789–795, June, 1990.

We thank A. N. Sobolev for assistance in calculating the structure of (III).

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Andrievskii, A.M., Chelysheva, O.V., Poplavskii, A.N. et al. Synthesis and structure of bromonitro-6(5H)-phenanthridinones. Chem Heterocycl Compd 26, 658–663 (1990). https://doi.org/10.1007/BF00756418

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  • DOI: https://doi.org/10.1007/BF00756418

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