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 - 2010/9/30
Y1 - 2010/9/30
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.
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U2 - 10.1055/s-0030-1257909
DO - 10.1055/s-0030-1257909
M3 - Article
AN - SCOPUS:77957168961
SP - 3339
EP - 3345
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 19
M1 - M02010SS
ER -