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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 351–354 | Cite as

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

  • Mohammad Hosein SayahiEmail author
  • Mehdi Khoshneviszadeh
  • Mehdi Soheilizad
  • Seyyed Jafar SaghanezhadEmail author
  • Mohammad Mahdavi
Article

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.

Keywords

2-arylbenzimidazoles benzamidine hydrochloride 1-fluoro-2-nitrobenzene copper-catalyzed reactions 

Notes

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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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Mohammad Hosein Sayahi
    • 1
    Email author
  • Mehdi Khoshneviszadeh
    • 2
  • Mehdi Soheilizad
    • 3
  • Seyyed Jafar Saghanezhad
    • 4
    Email author
  • Mohammad Mahdavi
    • 5
  1. 1.Department of ChemistryPayame Noor University (PNU)TehranIran
  2. 2.Medicinal & Natural Products Chemistry Research CenterShiraz University of Medical SciencesShirazIran
  3. 3.CinnaGen Medical Biotechnology Research CenterAlborz University of Medical SciencesKarajIran
  4. 4.ACECR-Production Technology Research InstituteAhvazIran
  5. 5.Endocrinology and Metabolism Research Center, Endocrinology and MetabolismClinical Sciences Institute Tehran University of Medical SciencesTehranIran

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