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

Klaus Banert; Jens Wutke; Tobias Rüffer; Heinrich Lang

doi:10.1055/s-2008-1078602

PAPER

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 Wutke^a, Tobias Rüffer^b, Heinrich Lang^b
^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

Abstract

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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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References

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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).

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