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Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen

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Abstract

A facile synthesis of para-quinones derived from fused benzimidazoles with a bridgehead nitrogen atom was developed. The heterocyclic quinone core formed as a result of reductive cyclization of ortho-nitroarenes containing alicyclic and aromatic azaheterocycles. Functionalization of 1,2,3,4-tetrahydro- and pyrido[1,2-a]benzimidazoles via SEAr, condensation, and reduction reactions allowed synthesis of amino derivatives which were oxidized with KNO3 in H2SO4 to obtain novel heterocyclic quinones.

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 18-33-00003).

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Authors and Affiliations

  1. Demidov Yaroslavl State University, 150003, Yaroslavl, Russia

    R. S. Begunov & A. A. Sokolov

  2. Yaroslavl State Technical University, 150023, Yaroslavl, Russia

    S. I. Filimonov

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  1. R. S. Begunov
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  2. A. A. Sokolov
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Correspondence to R. S. Begunov.

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Begunov, R.S., Sokolov, A.A. & Filimonov, S.I. Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen. Russ J Org Chem 56, 1383–1391 (2020). https://doi.org/10.1134/S1070428020080084

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