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Reactivity of 4,9-diazapyrene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Heating 5,10-dimethyl-4,9-diazapyrene with nitric acid to 200°C does not bring about disruption of the heteroring but leads to the formation of nitro derivatives of 5,10-dioxo-4,5,9,10-tetrahydro-4,9-diazapyrene. 4,9-Diazapyrene is a weak base that forms quaternary salts only under severe conditions. Piperidine replaces two chlorine atoms in 5,10-dichloro-4,9-diazapyrene, whereas only monosubstitution occurs in the case of 1,6-dibromo-5,10-dimethyl-4,9-diazapyrene. Calculations by the Hückel MO method, in agreement with the experimental data, characterize 4,9-diazapyrene as a strong electron acceptor and indicate that the effect of conjugation is propagated primarily along the periphery of the molecule rather than between the heterorings.

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Authors and Affiliations

  1. Leningrad Branch, All-Union Scientific-Research Institute of Synthetic Fibers, Leningrad

    K. V. Veksler & L. S. Éfros

Authors
  1. K. V. Veksler
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  2. L. S. Éfros
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 683–689, May, 1975.

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Veksler, K.V., Éfros, L.S. Reactivity of 4,9-diazapyrene. Chem Heterocycl Compd 11, 594–599 (1975). https://doi.org/10.1007/BF00480487

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  • DOI: https://doi.org/10.1007/BF00480487

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