1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines – combined experimental and theoretical studies

  1. Aleksey Yu VorobevORCID Logo,
  2. Gennady I. BorodkinORCID Logo,
  3. Rodion V. AndreevORCID Logo and
  4. Vyacheslav G. Shubin

Submitting author affiliation: Novosibirsk Institute of Organic Chemistry, Novosibirsk, Russian Federation

Beilstein Arch. 2020, 202022. https://doi.org/10.3762/bxiv.2020.22.v1

Published 20 Feb 2020

  • Preprint


Series of 2-pyridyl substituted [1,2,4]triazolo[1,5-a]azines have been synthesized by reaction of cyanopyridines with N-aminoazinium mesitylenesulfonates under basic conditions. The reaction proceeds smoothly with pyridinium, 1,10-phenanthrolinium and 8-oxyquinolinium salts. In case of quinolinium and isoquinolinium salts dimers of corresponding N-imines were isolated. Pyrazinium- and pyridazinium-N-imines didn’t possess any reactivity toward cyanopyridines. DFT studies give high activation barriers for 4-cyanopyridine cycloaddition to quinolinium and pyrazinium-N-imnes as well as highly negative free energy of dimerisation for quinolinium and isoquinolinium-N-imnes.

Keywords: DFT;1,3-dipolar cycloaddition; N-imines; [1,2,4]triazolo[1,5-a]azines

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Vorobev, A. Y.; Borodkin, G. I.; Andreev, R. V.; Shubin, V. G. Beilstein Arch. 2020, 202022. doi:10.3762/bxiv.2020.22.v1

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