James T. Fletcher, Matthew E. Keeney, Sara E. Walz
Sep 30, 2010
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Influential Citations
36
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Journal
Synthesis
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.