ATOM-EFFICIENT SYNTHESIS OF HYBRID MOLECULES COMBINING FRAGMENTS OF TRIAZOLOPYRIMIDINES AND 3-ETHOXYCARBONYL-1-ETHYL-6-FLUOROQUINOLIN-4(1<i>H</i>)-ONE THROUGH 1,2,3-TRIAZOLE LINKER

Authors

  • Konstantin V. Savateev Department of Organic and Biomolecular Chemistry, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Pavel A. Slepukhin Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620137, Russia
  • Svetlana K. Kotovskaya Department of Organic and Biomolecular Chemistry, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Valery N. Charushin Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620137, Russia
  • Vladimir L. Rusinov Department of Organic and Biomolecular Chemistry, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Oleg N. Chupakhin Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620137, Russia

DOI:

https://doi.org/10.1007/5958

Keywords:

fluoroquinolones, nitro compounds, [1, 2, 4]triazolo[1, 5-a]pyrimidines, azide-alkyne cycloaddition, chlorodeoxygenation, click chemistry, cyclization, hybrid molecules.

Abstract

An atom-efficient method toward hybrid molecules via azide-alkyne cycloaddition of 7-azido-3-ethoxycarbonyl-1-ethyl-6-fluoroquinolin-4(1H)-one and novel perspective triazolopyrimidines has been developed. This procedure features mild conditions and a broad substrate scope including hydrophobic and hydrophilic triazolopyrimidines. The synthesized hybrid structures combine fragments of fluoroquinolone with proved antibacterial activity and triazolopyrimidines, which may act as structural analogs of adenosine receptor effectors or antiviral azoloazine heterocycles.

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Published

2021-02-22

Issue

Vol. 57 No. 2 (2021)

Section

Original Papers