1,3-DIPOLAR CYCLOADDITION OF CYANOPYRIDINES TO HETEROCYCLIC <i>N</i>-IMINES: EXPERIMENTAL AND THEORETICAL STUDY

Authors

  • Aleksey Yu. Vorob'ev N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia Novosibirsk State University, 1 Pirogov St., Novosibirsk 630090, Russia
  • Gennady I. Borodkin N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia Novosibirsk State University, 1 Pirogov St., Novosibirsk 630090, Russia
  • Rodion V. Andreev N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Vyacheslav G. Shubin N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

DOI:

https://doi.org/10.1007/5903

Keywords:

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

Abstract

Series of 2-pyridyl[1,2,4]triazolo[1,5-a]azines have been synthesized by cycloaddition of cyanopyridines with N-aminoazinium mesitylenesulfonates
under basic conditions (KOH/H2O). An improved protocol for pyridyl-substituted [1,2,4]triazolo[1,5-a]pyridines synthesis based on addition of H2O2 as internal oxidant has been suggested. In the case of quinolinium and isoquinolinium salts, only dimerization of the corresponding N-imines has been observed, while pyrazinium-N-imine has not shown any reactivity toward cycloaddition. DFT studies have shown that the cycloaddition proceeds through concerted mechanism.

Author Biography

Aleksey Yu. Vorob'ev, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia Novosibirsk State University, 1 Pirogov St., Novosibirsk 630090, Russia

Лаборатория фотокатализа, с.н.с., завлаб

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Published

2021-03-15

Issue

Vol. 57 No. 3 (2021)

Section

Original Papers