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Synthesis
DOI: 10.1055/a-2649-0022
Paper

Synthesis of Novel Imido-Substituted 1,4-Naphthoquinones and Benzoquinone Derivatives

Authors

  • Daichi Uchida

    1   Graduate School of Agriculture, Department of Applied Biological Chemistry, Osaka Metropolitan University, Sakai, Japan (Ringgold ID: RIN12936)

  • Haruhiko Kobayashi

    1   Graduate School of Agriculture, Department of Applied Biological Chemistry, Osaka Metropolitan University, Sakai, Japan (Ringgold ID: RIN12936)

  • Michiko Nagai

    1   Graduate School of Agriculture, Department of Applied Biological Chemistry, Osaka Metropolitan University, Sakai, Japan (Ringgold ID: RIN12936)

  • Shinji Tanimori

    1   Graduate School of Agriculture, Department of Applied Biological Chemistry, Osaka Metropolitan University, Sakai, Japan (Ringgold ID: RIN12936)

We gratefully acknowledge the financial support from JSPS KAKENHI Grant Number 23K05060 (S.T.).
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Graphical Abstract

Abstract

Imido-substituted 2-bromo-1,4-naphthoquinones and benzoquinone have been formed from quinones and N-bromosuccinimide in the presence of DABCO under mild conditions. The reaction seems to proceed through a partially radical pathway based on control experiments. Nucleophilic addition–eliminations of imidated quinones have occurred smoothly to provide a new class of substituted quinone derivatives in good yields.

Keywords

Naphthoquinone - Benzoquinone - N-bromosuccinimide - DABCO - Radical reaction

Supplementary Material



Publication History

Received: 06 May 2025

Accepted after revision: 03 July 2025

Accepted Manuscript online:
03 July 2025

Article published online:
26 November 2025

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