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Reaction of 2-Aminobenzimidazoles with Acetylene in the KOBut/DMSO System. Self-Assembly of Benzo[d]imidazo[1,2-a]imidazoles and Benzo[4,5]imidazo[1,2-a]pyrimidines under Competition between Nucleophilic Centers

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Abstract

2-Aminobenzimidazoles react with acetylene in the KOBut/DMSO superbase system (80°C, 20 min) to give benzimidazo[1,2-a]imidazoles and benzimidazo[1,2-a]pyrimidines formed by the self-assembly of the starting compounds with two or three molecules of acetylene. Vinyl derivatives of 1,3-dihydro-2H-benz[d]imidazole-2-imine were also isolated.

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ACKNOWLEDGMENTS

The spectra were obtained using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

Funding

The work was financially supported by the Russian Science Foundation (project no. 19-13-00052).

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    N. V. Semenova, I. A. Ushakov, E. Yu. Schmidt & B. A. Trofimov

  2. Angarsk State Technical University, 665835, Angarsk, Russia

    E. Yu. Schmidt

Authors
  1. N. V. Semenova
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  2. I. A. Ushakov
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  3. E. Yu. Schmidt
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  4. B. A. Trofimov
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Correspondence to B. A. Trofimov.

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Semenova, N.V., Ushakov, I.A., Schmidt, E.Y. et al. Reaction of 2-Aminobenzimidazoles with Acetylene in the KOBut/DMSO System. Self-Assembly of Benzo[d]imidazo[1,2-a]imidazoles and Benzo[4,5]imidazo[1,2-a]pyrimidines under Competition between Nucleophilic Centers. Russ J Org Chem 60, 353–357 (2024). https://doi.org/10.1134/S1070428024020192

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