Abstract
A series of 1-allylated and 1-benzylated 1,2,3-triazoles with varying substituents at the 4-position were prepared in yields ranging from 74-98% using a two-step one-pot click transformation. This tandem reaction involved the nucleophilic substitution of allyl chloride and benzyl bromide with sodium azide to form organic azide intermediates followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition with alkyne reactants in a single reaction pot without the need for sequentially separating reaction steps. 1-Allyl- and 1-benzyl-4-alkyl-1,2,3-triazoles possessing linear alkyl chains underwent efficient N-alkylation at the 3-position with methyl iodide, while tert-butyl and phenyl derivatives did not. Each of the 1-allyl- and 1-benzyl-3-methyl-4- alkyl-1,2,3-triazolium iodide salts prepared was a viscous liquid at room temperature with a stable shelf life.
| Original language | English |
|---|---|
| Article number | M02010SS |
| Pages (from-to) | 3339-3345 |
| Number of pages | 7 |
| Journal | Synthesis |
| Issue number | 19 |
| DOIs | |
| State | Published - 2010 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Organic Chemistry
- Catalysis
Cite this
1-Allyl- and 1-benzyl-3-methyl-1,2,3-triazolium salts via tandem click transformations. / Fletcher, James T.; Keeney, Matthew E.; Walz, Sara E.
In: Synthesis, No. 19, M02010SS, 2010, p. 3339-3345.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 1-Allyl- and 1-benzyl-3-methyl-1,2,3-triazolium salts via tandem click transformations
AU - Fletcher, James T.
AU - Keeney, Matthew E.
AU - Walz, Sara E.
PY - 2010
Y1 - 2010
N2 - A series of 1-allylated and 1-benzylated 1,2,3-triazoles with varying substituents at the 4-position were prepared in yields ranging from 74-98% using a two-step one-pot click transformation. This tandem reaction involved the nucleophilic substitution of allyl chloride and benzyl bromide with sodium azide to form organic azide intermediates followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition with alkyne reactants in a single reaction pot without the need for sequentially separating reaction steps. 1-Allyl- and 1-benzyl-4-alkyl-1,2,3-triazoles possessing linear alkyl chains underwent efficient N-alkylation at the 3-position with methyl iodide, while tert-butyl and phenyl derivatives did not. Each of the 1-allyl- and 1-benzyl-3-methyl-4- alkyl-1,2,3-triazolium iodide salts prepared was a viscous liquid at room temperature with a stable shelf life.
AB - A series of 1-allylated and 1-benzylated 1,2,3-triazoles with varying substituents at the 4-position were prepared in yields ranging from 74-98% using a two-step one-pot click transformation. This tandem reaction involved the nucleophilic substitution of allyl chloride and benzyl bromide with sodium azide to form organic azide intermediates followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition with alkyne reactants in a single reaction pot without the need for sequentially separating reaction steps. 1-Allyl- and 1-benzyl-4-alkyl-1,2,3-triazoles possessing linear alkyl chains underwent efficient N-alkylation at the 3-position with methyl iodide, while tert-butyl and phenyl derivatives did not. Each of the 1-allyl- and 1-benzyl-3-methyl-4- alkyl-1,2,3-triazolium iodide salts prepared was a viscous liquid at room temperature with a stable shelf life.
UR - http://www.scopus.com/inward/record.url?scp=77957168961&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77957168961&partnerID=8YFLogxK
U2 - 10.1055/s-0030-1257909
DO - 10.1055/s-0030-1257909
M3 - Article
SP - 3339
EP - 3345
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 19
M1 - M02010SS
ER -