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Synthesis 2010(19): 3339-3345  
DOI: 10.1055/s-0030-1257909
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

1-Allyl- and 1-Benzyl-3-methyl-1,2,3-triazolium Salts via Tandem Click Transformations

James T. Fletcher*, Matthew E. Keeney, Sara E. Walz
Department of Chemistry, Creighton University, Omaha, NE 68178, USA
Fax: +1(402)2805737; e-Mail: jamesfletcher@creighton.edu;
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Publication History

Received 9 March 2010
Publication Date:
22 July 2010 (online)

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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.

Key words

alkynes - azides - cycloaddition - ionic liquids - tandem reaction