Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines

A One-Pot Approach

Kseniya D. Gavlik, Svetlana G. Lesogorova, Ekaterina S. Sukhorukova, Julia O. Subbotina, Pavel A. Slepukhin, Enrico Benassi, Nataliya P. Belskaya

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A one-pot approach for the synthesis of 2-aryl-5-amino-1,2,3-triazoles is reported. This approach involves a tandem nucleophilic addition of alkylamines to hydrazonoyl cyanides and in situ oxidative cyclization of the resulting 2-(arylazo)ethene-1,1-diamines in the presence of copper(II) acetate and air. The described one-pot procedure is characterized by good yields, excellent selectivity, methodical simplicity, and uses readily available chemicals. This method was applied to the gram-scale synthesis of 2-aryl-1,2,3-triazoles. A new one-pot synthesis of functionalized 2-aryl-1,2,3-triazoles has been developed. The developed procedure is efficient, safe and applicable to a broad scope of substrates. In addition, tethis approach has a higher atom economy factor and allows for the synthesis of new 2-aryl-1,2,3-triazoles that were not previously accessible using reported methods.

Original languageEnglish
Pages (from-to)2700-2710
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number15
DOIs
Publication statusPublished - 1 May 2016
Externally publishedYes

Fingerprint

Triazoles
Diamines
Cyclization
diamines
synthesis
Cyanides
cyanides
economy
acetates
selectivity
copper
Atoms
ethylene
air
Substrates
Air
atoms

Keywords

  • Hydrazones
  • Nitrogen heterocycles
  • Nucleophilic addition
  • Oxidative cyclization
  • Regioselectivity
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Gavlik, K. D., Lesogorova, S. G., Sukhorukova, E. S., Subbotina, J. O., Slepukhin, P. A., Benassi, E., & Belskaya, N. P. (2016). Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines: A One-Pot Approach. European Journal of Organic Chemistry, 2016(15), 2700-2710. https://doi.org/10.1002/ejoc.201600256

Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines : A One-Pot Approach. / Gavlik, Kseniya D.; Lesogorova, Svetlana G.; Sukhorukova, Ekaterina S.; Subbotina, Julia O.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.

In: European Journal of Organic Chemistry, Vol. 2016, No. 15, 01.05.2016, p. 2700-2710.

Research output: Contribution to journalArticle

Gavlik, KD, Lesogorova, SG, Sukhorukova, ES, Subbotina, JO, Slepukhin, PA, Benassi, E & Belskaya, NP 2016, 'Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines: A One-Pot Approach', European Journal of Organic Chemistry, vol. 2016, no. 15, pp. 2700-2710. https://doi.org/10.1002/ejoc.201600256
Gavlik, Kseniya D. ; Lesogorova, Svetlana G. ; Sukhorukova, Ekaterina S. ; Subbotina, Julia O. ; Slepukhin, Pavel A. ; Benassi, Enrico ; Belskaya, Nataliya P. / Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines : A One-Pot Approach. In: European Journal of Organic Chemistry. 2016 ; Vol. 2016, No. 15. pp. 2700-2710.
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