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Opianic Acid in the Synthesis of Benzimidazole Derivatives

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Chemistry of Natural Compounds Aims and scope

Heating an equimolar mixture of opianic acid and o-phenylenediamine in MeOH or EtOH produced 2-(2-carboxy-3,4-dimethoxyphenyl)benzimidazole, which was readily dehydrated in refluxing acetic or propionic anhydride to 11H-1,2-dimethoxyisoindolo[2,3-a]benzimidazol-11-one. Analogous reactions were carried out with 4,5-dichloro-o-phenylenediamine.

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Notes

  1. IR spectrum (ν, cm–1): 3470 (NH), 3373 (NH2, as), 3308 (NH2, s), 1736 (C=O), 1034 (C-O-C, as), 855 (C-O-C, s).

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Acknowledgment

Spectral studies used equipment at the Molecular Spectroscopy CCU, SFU. The work was supported financially by the RF Ministry of Education and Science (project part of a state task for scientific activity of SFU, topic No. 4.967.2014/K).

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Prosp. Stachki, Rostov-on-Don, 344090, Russian Federation

    G. S. Borodkin, L. Yu. Ukhin, L. V. Belousova & A. V. Alekseenko

  2. Southern Scientific Center, Russian Academy of Sciences, 41 Chekhov St., Rostov-on-Don, 344006, Russian Federation

    E. N. Shepelenko

Authors
  1. G. S. Borodkin
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  2. L. Yu. Ukhin
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  3. L. V. Belousova
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  4. E. N. Shepelenko
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  5. A. V. Alekseenko
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Correspondence to L. Yu. Ukhin.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 99–101.

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Borodkin, G.S., Ukhin, L.Y., Belousova, L.V. et al. Opianic Acid in the Synthesis of Benzimidazole Derivatives. Chem Nat Compd 53, 118–120 (2017). https://doi.org/10.1007/s10600-017-1923-5

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  • DOI: https://doi.org/10.1007/s10600-017-1923-5

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