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Rearrangement of 3-(bromomethyl)quinoxalin-2(1H)-ones when exposed to 2-aminopyridines as a new method for the synthesis of 2-(imidazo[1,2-a]pyridin-2-yl)benzimidazoles

  • N. A. Zhukova,
  • D. S. Perevalova,
  • V. V. Syakaev,
  • T. N. Beschastnova,
  • A. T. Gubaidullin,
  • O. G. Sinyashin,
  • V. A. Mamedov

摘要

A new efficient method was developed for the synthesis of 2-(imidazo[1,2-a]pyridin-2-yl)benzimidazoles based on the Mamedov rearrangement. The key step of the synthesis involves the acid-catalyzed rearrangement of spiroquinoxalinone derivatives as intramolecular cyclization products of 2-amino-1-[(quinoxalin-2(1H)-on-3-yl]methyl)pyridinium salts, which are generated by the modified Chichibabin reaction.