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Issue 8, 2010
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Synthesis of triazolyl methyl-substituted amino- and oxy-undecahydrododecaborates for potential application in boron neutron capture therapy

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Abstract

A general approach to the synthesis of triazole conjugates containing undecahydro-closo-dodecaborate anions based on Huisgen 1,3-dipolar cycloaddition is presented. Undecahydro-closo-dodecaborate anions bearing terminal alkyne groups were synthesized by the reaction of H3N–B12H11 or HO–B12H112− with alkyne halides in N,N-dimethylformamide using KOH as a base. Variation of reaction time, alkyne halide concentration and steric demands of the alkyne halide resulted in the stepwise introduction of one to three alkyne groups into H3N–B12H11. Two compounds {(CH[triple bond, length as m-dash]CCH2)3N–B12H11 and (CH[triple bond, length as m-dash]CCH2)O–B12H112−} were crystallized for single-crystal X-ray diffraction studies. N- and O-alkyne undecahydro-closo-dodecaborate anions reacted with various functionalized azides including lipid, carborane, aryl and hydroxyalkyl groups. The current study provides various synthetic applications not only for BNCT but also for boron cluster materials.

Graphical abstract: Synthesis of triazolyl methyl-substituted amino- and oxy-undecahydrododecaborates for potential application in boron neutron capture therapy

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Publication details

The article was received on 21 Jan 2010, accepted on 22 Feb 2010 and first published on 13 Apr 2010


Article type: Paper
DOI: 10.1039/C0NJ00046A
Citation: New J. Chem., 2010,34, 1612-1622
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    Synthesis of triazolyl methyl-substituted amino- and oxy-undecahydrododecaborates for potential application in boron neutron capture therapy

    M. E. El-Zaria, A. R. Genady and H. Nakamura, New J. Chem., 2010, 34, 1612
    DOI: 10.1039/C0NJ00046A

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