Russian Chemical Bulletin

, Volume 58, Issue 9, pp 1986–1990 | Cite as

A novel rearrangement in the system 3-[aryl(chloro)methyl]quinoxalin-2(1H)-one— α-picoline as a simple and efficient route to indolizin-2-ylbenzimidazoles

  • V. A. Mamedov
  • D. F. Saifina
  • A. T. Gubaidullin
  • A. F. Saifina
  • I. Kh. Rizvanov
  • V. R. Ganieva
Full Articles


A reaction of 3-(α-chlorobenzyl)quinoxalin-2(1 H)-one with α-picoline gives 2-(3-phenyl-indolizin-2-yl)benzimidazole as a result of a ring-contracting rearrangement involving the fragment C(2)—C(3)—C(Cl)Ph of the quinoxaline system and the fragment N=CH—Me of the α-picoline system. Possible pathways of this reaction are discussed.

Keywords 3-(α-chlorobenzyl)quinoxalin-2(1 H)-one α-picoline ring contraction rearrangement 2-(3-phenylindolizin-2-yl)benzimidazole IR spectroscopy 1H NMR spectroscopy X-ray diffraction analysis 


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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • V. A. Mamedov
    • 1
  • D. F. Saifina
  • A. T. Gubaidullin
  • A. F. Saifina
  • I. Kh. Rizvanov
  • V. R. Ganieva
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Research Center of the Russian Academy of SciencesKazanRussian Federation

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