Выдержка
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.
| Язык оригинала | Английский |
|---|---|
| Страницы (с-по) | 2700-2710 |
| Число страниц | 11 |
| Журнал | European Journal of Organic Chemistry |
| Том | 2016 |
| Номер выпуска | 15 |
| DOI | |
| Состояние | Опубликовано - 1 мая 2016 |
| Опубликовано для внешнего пользования | Да |
Отпечаток
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Цитировать
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.
В: European Journal of Organic Chemistry, Том 2016, № 15, 01.05.2016, стр. 2700-2710.Результат исследований: Материалы для журнала › Статья
}
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
AN - SCOPUS:84964669275
VL - 2016
SP - 2700
EP - 2710
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 15
ER -