Abstract
The "click chemistry" of using organic azides and terminal alkynes is arguably the most efficient and straightforward route to the synthesis of 1,2,3-triazoles. In this paper, an alternative and direct access to ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate is described. Treatment of ethyl diazoacetate with 4-methoxyaniline derived aryl imines in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene provided fully substituted 1,2,3-triazoles in good to high chemical yields. The basemediated reaction tolerates various substituted phenyl imines as well as ethyl diazoacetate or the more bulky diazoacetamide. A reasonable mechanism is proposed that involves the addition of an imine nitrogen atom to the terminal nitrogen atom of the diazo compound, followed by aromatization to give the 1,2,3-triazole. The presence of the 4-carboxy group is advantageous as it can be easily transformed into other functional groups.
| Original language | English |
|---|---|
| Pages (from-to) | 328-333 |
| Number of pages | 6 |
| Journal | Chemistry - An Asian Journal |
| Volume | 5 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2010 Feb 1 |
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Keywords
- Aromaticity
- Cycloaddition
- Diazo compounds
- Heterocycles
- Triazoles
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
Cite this
An efficient and convenient synthesis of ethyl 1-(4-Methoxyphenyl)-5- phenyl-1H-1,2,3-triazole-4-carboxylate. / Chen, Jung Hsuan; Liu, Shuan Ru; Chen, Kwunmin.
In: Chemistry - An Asian Journal, Vol. 5, No. 2, 01.02.2010, p. 328-333.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An efficient and convenient synthesis of ethyl 1-(4-Methoxyphenyl)-5- phenyl-1H-1,2,3-triazole-4-carboxylate
AU - Chen, Jung Hsuan
AU - Liu, Shuan Ru
AU - Chen, Kwunmin
PY - 2010/2/1
Y1 - 2010/2/1
N2 - The "click chemistry" of using organic azides and terminal alkynes is arguably the most efficient and straightforward route to the synthesis of 1,2,3-triazoles. In this paper, an alternative and direct access to ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate is described. Treatment of ethyl diazoacetate with 4-methoxyaniline derived aryl imines in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene provided fully substituted 1,2,3-triazoles in good to high chemical yields. The basemediated reaction tolerates various substituted phenyl imines as well as ethyl diazoacetate or the more bulky diazoacetamide. A reasonable mechanism is proposed that involves the addition of an imine nitrogen atom to the terminal nitrogen atom of the diazo compound, followed by aromatization to give the 1,2,3-triazole. The presence of the 4-carboxy group is advantageous as it can be easily transformed into other functional groups.
AB - The "click chemistry" of using organic azides and terminal alkynes is arguably the most efficient and straightforward route to the synthesis of 1,2,3-triazoles. In this paper, an alternative and direct access to ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate is described. Treatment of ethyl diazoacetate with 4-methoxyaniline derived aryl imines in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene provided fully substituted 1,2,3-triazoles in good to high chemical yields. The basemediated reaction tolerates various substituted phenyl imines as well as ethyl diazoacetate or the more bulky diazoacetamide. A reasonable mechanism is proposed that involves the addition of an imine nitrogen atom to the terminal nitrogen atom of the diazo compound, followed by aromatization to give the 1,2,3-triazole. The presence of the 4-carboxy group is advantageous as it can be easily transformed into other functional groups.
KW - Aromaticity
KW - Cycloaddition
KW - Diazo compounds
KW - Heterocycles
KW - Triazoles
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UR - http://www.scopus.com/inward/citedby.url?scp=76149124248&partnerID=8YFLogxK
U2 - 10.1002/asia.200900320
DO - 10.1002/asia.200900320
M3 - Article
C2 - 20029887
AN - SCOPUS:76149124248
VL - 5
SP - 328
EP - 333
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 2
ER -