THE DIMROTH REARRANGEMENT OF 5-AMINO-1-ARYL-1,2,3-TRIAZOLE-4-CARBOTHIOAMIDES

Authors

  • Владимир Г. Илькин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Лидия Н. Дианова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Василий А. Бакулев Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Вера С. Берсенева Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Дмитрий А. Савельев Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Татьяна В. Березкина Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia

DOI:

https://doi.org/10.1007/5720

Keywords:

azides, thioamides, 1, 2, 3-triazoles, Dimroth rearrangement.

Abstract

The rearrangement of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides was investigated. The process was optimized by varying the solvent, temperature, and the type of base. The optimal reaction conditions were found, and new 1-unsubstituted 5-arylamino-1,2,3-triazole-4-carbothioamides were synthesized. It has been shown that 1-aryl-1,2,3-triazoles containing a nitro group in the para position undergo rearrangement upon heating under reflux in n-butanol in the absence of a base. The rearrangement of compounds containing halogen, hydrogen, methyl, or methoxy groups in the aryl moiety requires the use of a base. The structure of the obtained compounds was confirmed by the data of NMR spectroscopy and mass spectrometry.

Author Biography

Владимир Г. Илькин, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia

The chief of the technologyfor Organic Synthesis Department

Published

2020-11-05

Issue

Section

Original Papers