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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 5, pp 568–574 | Cite as

2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides 7*. Synthesis of 4-amino-1-aryl-6-halo-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-с]pyridine-7-carbonitriles

  • Yakov S. Kayukov
  • Sergey V. KarpovEmail author
  • Arthur A. Grigor’ev
  • Anastasiya L. Nikiforova
  • Oleg E. Nasakin
  • Ekaterina S. Shchegravina
  • Olga V. Kayukova
  • Victor A. Tafeenko
Article

The reaction of 2-acyl(aroyl)-1,1,3,3-tetracyanopropenides with gaseous hydrogen halides was used to obtain 2-amino-3-aroyl(acyl)-6-halopyridine-3,5-dicarbonitriles, which were subsequently converted to the respective 4-amino-1-aryl-6-halo-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles by treatment with concentrated sulfuric acid, followed by aqueous workup.

Keywords

pyridines pyrrolo[3,4-с]pyridines tetracyanopropenides annulation iminolactone–lactam rearrangement 

Notes

Acknowledgements

This work was performed with support from the Scholarship of the President of the Russian Federation for young scientists and doctoral students SP-3725.2015.4.

X-ray structural analysis was performed with support from the program for development of the M. V. Lomonosov Moscow State University.

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Yakov S. Kayukov
    • 1
  • Sergey V. Karpov
    • 1
    Email author
  • Arthur A. Grigor’ev
    • 1
  • Anastasiya L. Nikiforova
    • 1
  • Oleg E. Nasakin
    • 1
  • Ekaterina S. Shchegravina
    • 2
  • Olga V. Kayukova
    • 3
  • Victor A. Tafeenko
    • 4
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia
  2. 2.N. I. Lobachevsky State University of Nizhny NovgorodNizhny NovgorodRussia
  3. 3.Chuvash State Agricultural AcademyCheboksaryRussia
  4. 4.M. V. Lomonosov Moscow State UniversityMoscowRussia

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