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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 739–747 | Cite as

Nucleophilic addition of amide anions to 1-methyl-5(6,7,8)-nitroquinolinium salts

  • Elena K. Avakyan
  • Gulminat А. Amangasieva
  • Oleg P. Demidov
  • Anastasia А. Borovleva
  • Elena S. Beketova
  • Oksana А. Nechaeva
  • Ivan V. BorovlevEmail author
Article
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The stable adducts, N-(1-methyl-5(6,7,8)-nitro-1,2-dihydroquinolin-2-yl)benzamides were synthesized for the first time by the action of amide anions of aromatic acids on the N-methyl salts of 5-, 6-, 7-, and 8-nitroquinolines in anhydrous MeCN. Oxidative dehydrogenation of these amides afforded aroylimino derivatives of the corresponding 1-methyl-5(6,7,8)-nitro-2-quinolones.

Keywords

nitroquinoline N-methyl cations nitroquinolines nucleophilic addition 

Notes

This work was financially supported by the Ministry of Education and Science of the Russian Federation as part of the State assignment (project № 4.6306.2017/8.9).

Supplementary material

10593_2019_2529_MOESM1_ESM.pdf (4.6 mb)
ESM 1 (PDF 4660 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Elena K. Avakyan
    • 1
  • Gulminat А. Amangasieva
    • 1
  • Oleg P. Demidov
    • 1
  • Anastasia А. Borovleva
    • 1
  • Elena S. Beketova
    • 1
  • Oksana А. Nechaeva
    • 1
  • Ivan V. Borovlev
    • 1
    Email author
  1. 1.North Caucasus Federal UniversityStavropolRussia

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