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 language | English |
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Pages (from-to) | 2700-2710 |
Number of pages | 11 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
Issue number | 15 |
DOIs | |
Publication status | Published - 1 May 2016 |
Externally published | Yes |
Keywords
- Hydrazones
- Nitrogen heterocycles
- Nucleophilic addition
- Oxidative cyclization
- Regioselectivity
- Synthetic methods
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry