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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

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Abstract

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.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. A. Mamedov

Authors
  1. V. A. Mamedov
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  2. D. F. Saifina
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  3. A. T. Gubaidullin
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  4. A. F. Saifina
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  5. I. Kh. Rizvanov
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  6. V. R. Ganieva
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Corresponding author

Correspondence to V. A. Mamedov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1924–1928, September, 2009.

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Mamedov, V.A., Saifina, D.F., Gubaidullin, A.T. et al. 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. Russ Chem Bull 58, 1986–1990 (2009). https://doi.org/10.1007/s11172-009-0271-4

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  • DOI: https://doi.org/10.1007/s11172-009-0271-4

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