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Synlett 2015; 26(08): 1045-1048
DOI: 10.1055/s-0034-1380164
DOI: 10.1055/s-0034-1380164
letter
Synthesis of Sulfur-Rich Crown Ethers via Azide–Alkyne Macrocyclization of α,ω-Diazido- and α,ω-Dipropargyl Sulfide Derivatives
Further Information
Publication History
Received: 09 December 2014
Accepted after revision: 22 January 2015
Publication Date:
27 February 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201508/lookinside/thumbnails/st-2014-b1018-l_10-1055_s-0034-1380164-1.jpg)
Abstract
A series of diazides and dithiols were prepared in a one-pot protocol from commercially available alcohols by a modified Appel reaction. Selected dithiols were converted into α,ω-dipropargyl sulfides and combined with thioglycol-derived diazides under Huisgen–Sharpless–Meldal reaction conditions to give a new class of 1,2,3-triazole-linked sulfur-rich crown ethers.
Key words
Appel reaction - click [3+2] cycloaddition - macrocycles - crown thioethers - thiiranium saltSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380164.
- Supporting Information
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References and Notes
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Diagnostic signals in 1H NMR spectra located at δ = 2.81–2.84, 2.93–2.98, and 3.76–3.78 ppm could be attributed to the methylene groups neighboring sulfur atom of the intermediates A according to the literature data: