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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 704–715 | Cite as

Synthesis of β-azolyl- and β-azolylcarbonylenamines and their reactions with aromatic azides

  • Yuri M. Shafran
  • Tetyana V. Beryozkina
  • Ilya V. Efimov
  • Vasiliy A. BakulevEmail author
Article
  • 18 Downloads

Synthesis of 4-acetyl-substituted azoles (1,2,3-triazole, 1,2,3-thiadiazole, and 1,2-oxazole) is reported. Organocatalytic reactions of 4-acetyl-1,2,3-triazoles with aryl azides were used to obtain bis-1,2,3-triazoles containing directly linked ring systems. The reactions of 4-acetylazoles with DMF–DMA led to the formation of enamines. It was found that the acetyl and methyl groups in 4-acetyl-5-methyl-1,2,3-thiadiazole competed for the role of reactive site. The obtained enamines reacted with aryl azides, forming bisheterocycles that were linked by a carbonyl group. The structures of the synthesized compounds were proved by NMR spectroscopy, mass spectrometry, and X-ray structural analysis.

Keywords

bistriazoles enamines enaminones 1,2-oxazoles 1,2,3-thiadiazoles 1,2,3-triazoles 

Supplementary material

10593_2019_2525_MOESM1_ESM.pdf (702 kb)
ESM 1 (PDF 702 kb)

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Copyright information

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

Authors and Affiliations

  • Yuri M. Shafran
    • 1
  • Tetyana V. Beryozkina
    • 1
  • Ilya V. Efimov
    • 1
  • Vasiliy A. Bakulev
    • 1
    Email author
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia

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