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Efficient copper-catalyzed synthesis of 2-arylbenzimidazole derivatives by reaction of 1-fluoro-2-nitrobenzene with benzamidine hydrochlorides

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Chemistry of Heterocyclic Compounds Aims and scope

A novel and efficient approach to the preparation of 2-arylbenzimidazoles is described. Heating a mixture of 1-fluoro-2-nitrobenzene and benzamidine hydrochlorides in the presence of CuBr and K2CO3 in DMSO afforded 2-arylbenzimidazoles in good to excellent yields. The reaction was initiated by nucleophilic aromatic substitution and further proceeded by intramolecular nucleophilic copper-catalyzed cyclization reaction of benzamidine.

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The authors wish to thank the support of the Vice-Chancellor for Research of Shiraz University of Medical Sciences (grant No. 1396-01-12-14909).

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran

    Mohammad Hosein Sayahi

  2. Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

    Mehdi Khoshneviszadeh

  3. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

    Mehdi Soheilizad

  4. ACECR-Production Technology Research Institute, Ahvaz, Iran

    Seyyed Jafar Saghanezhad

  5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism, Clinical Sciences Institute Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Mahdavi

Authors
  1. Mohammad Hosein Sayahi
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  2. Mehdi Khoshneviszadeh
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  3. Mehdi Soheilizad
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  4. Seyyed Jafar Saghanezhad
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  5. Mohammad Mahdavi
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Corresponding authors

Correspondence to Mohammad Hosein Sayahi or Seyyed Jafar Saghanezhad.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 351–354

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Sayahi, M.H., Khoshneviszadeh, M., Soheilizad, M. et al. Efficient copper-catalyzed synthesis of 2-arylbenzimidazole derivatives by reaction of 1-fluoro-2-nitrobenzene with benzamidine hydrochlorides. Chem Heterocycl Comp 54, 351–354 (2018). https://doi.org/10.1007/s10593-018-2272-4

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  • DOI: https://doi.org/10.1007/s10593-018-2272-4

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