EFFICIENT COPPER-CATALYZED SYNTHESIS OF 2-ARYLBENZIMIDAZOLE DERIVATIVES BY REACTION OF 1-FLUORO-2-NITROBENZENE WITH BENZAMIDINE HYDROCHLORIDES

Authors

  • Mohammad Hosein Sayahi Payame Noor University (PNU)
  • Mehdi Khoshneviszadeh Shiraz University of Medical Sciences
  • Mehdi Soheilizad Alborz University of Medical Sciences
  • Seyyed Jafar Saghanezhad ACECR-Production Technology Research Institute
  • Mohammad Mahdavi Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences

DOI:

https://doi.org/10.1007/4391

Keywords:

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

Abstract

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.

Author Biographies

Mohammad Hosein Sayahi, Payame Noor University (PNU)

Department of Chemistry

Mehdi Khoshneviszadeh, Shiraz University of Medical Sciences

Medicinal & Natural Products Chemistry Research Center

Mehdi Soheilizad, Alborz University of Medical Sciences

CinnaGen Medical Biotechnology Research Center

Mohammad Mahdavi, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences

Endocrinology and Metabolism Research Center

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Published

2018-05-18

Issue

Vol. 54 No. 3 (2018): Metal-catalyzed synthesis of heterocycles

Section

Original Papers