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

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9 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

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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