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 |
|---|---|
| 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 |
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Keywords
- Hydrazones
- Nitrogen heterocycles
- Nucleophilic addition
- Oxidative cyclization
- Regioselectivity
- Synthetic methods
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines
T2 - A One-Pot Approach
AU - Gavlik, Kseniya D.
AU - Lesogorova, Svetlana G.
AU - Sukhorukova, Ekaterina S.
AU - Subbotina, Julia O.
AU - Slepukhin, Pavel A.
AU - Benassi, Enrico
AU - Belskaya, Nataliya P.
PY - 2016/5/1
Y1 - 2016/5/1
N2 - 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.
AB - 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.
KW - Hydrazones
KW - Nitrogen heterocycles
KW - Nucleophilic addition
KW - Oxidative cyclization
KW - Regioselectivity
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=84964669275&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84964669275&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201600256
DO - 10.1002/ejoc.201600256
M3 - Article
VL - 2016
SP - 2700
EP - 2710
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 15
ER -