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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 2, pp 167–171 | Cite as

Annulation of pyrrole ring in 4-acylpyridine-3,5-dicarbonitriles in the presence of ammonia

  • Arthur A. Grigor’evEmail author
  • Yakov S. Kayukov
  • Anastasiya L. Nikiforova
  • Sergey V. Karpov
  • Ekaterina S. Shchegravina
  • Olga V. Kayukova
  • Victor A. Tafeenko
Article
  • 26 Downloads

4-Acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles underwent heterocyclization in the presence of ammonia in aqueous dioxane medium, involving the ortho-ketonitrile fragment while preserving the halogen atom. The pyrrole ring annulation process proceeded regioselectively with the formation of a single positional isomer.

Keywords

pyridine-3,5-dicarbonitriles heteroannulation rearrangement regioselectivity 

Notes

This study received financial support from the Russian Foundation for Basic Research (project No. 18-33-01204 mol_a).

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

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Copyright information

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

Authors and Affiliations

  • Arthur A. Grigor’ev
    • 1
    Email author
  • Yakov S. Kayukov
    • 1
  • Anastasiya L. Nikiforova
    • 1
  • Sergey V. Karpov
    • 1
  • Ekaterina S. Shchegravina
    • 2
  • Olga V. Kayukova
    • 3
  • Victor A. Tafeenko
    • 4
  1. 1.Chuvash State University named after I. N. UlianovCheboksaryRussia
  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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