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Synthesis 2008(16): 2603-2609  
DOI: 10.1055/s-2008-1078602
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reactions of Unsaturated Azides; Part 22: [¹] The Alkyne Azide Click Chemistry as a Synthetic Tool for the Generation of Cage-Like Triazole Compounds

Klaus Banert*a, Jens Wutkea, Tobias Rüfferb, Heinrich Langb
a Chemnitz University of Technology, Institute of Chemistry, Organic Chemistry, Strasse der Nationen 62, 09111 Chemnitz, Germany
Fax: +49(371)53121229; e-Mail: klaus.banert@chemie.tu-chemnitz.de;
b Chemnitz University of Technology, Institute of Chemistry, Inorganic Chemistry, Strasse der Nationen 62, 09111 Chemnitz, Germany
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Publication History

Received 17 January 2008
Publication Date:
17 July 2008 (online)

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Abstract

The applicability of the copper(I)-catalyzed click reaction of terminal trialkynes with triazides to the synthesis of cage-like triazole compounds was determined. A number of starting materials were prepared and several monotriazoles as well as macrocyclic bistriazoles were obtained from the triazide trialkyne reaction. Finally, a tristriazole macrobicyclic compound was synthesized from the previously formed triazole precursors.

Key words

triazoles - cycloadditions - azides - alkynes - click chemistry

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29

Crystal data: C20H30N10O3, MW = 458.54, T = 100 K, λ = 0.71073 Å, triclinic, space group P1, a = 9.2764(11) Å, b = 10.7672(12) Å, c = 12.7431(10) Å, α = 75.015(8)˚, β = 81.255(8)˚, γ = 67.002(11)˚, V = 1129.9(2) Å3, Z = 2, D = 1.348 Mg/m3, µ = 0.096 mm-¹, F(000) = 488. Crystallographic data for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Centre under the number CCDC 673760. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).