Issue 32, 2015

Self-immolative base-mediated conjugate release from triazolylmethylcarbamates

Abstract

A range of carbamate functionalized 1,4-disubstituted triazoles featuring a base sensitive trigger residue, plus a model aromatic amine reporter group, were prepared via copper(I) catalysed azide–alkyne cycloaddition and evaluated for their self-immolative characteristics. This study revealed a clear structure–reactivity relationship, via Hammett analysis, between the structure of the 1,4-disubstituted triazole and the rate of self-immolative release of the amine reporter group, thus demonstrating that under basic conditions this type of triazole derivative has the potential to be employed in a range of chemical release systems.

Graphical abstract: Self-immolative base-mediated conjugate release from triazolylmethylcarbamates

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2015
Accepted
07 Jul 2015
First published
09 Jul 2015

Org. Biomol. Chem., 2015,13, 8703-8707

Self-immolative base-mediated conjugate release from triazolylmethylcarbamates

C. A. Blencowe, D. W. Thornthwaite, W. Hayes and A. T. Russell, Org. Biomol. Chem., 2015, 13, 8703 DOI: 10.1039/C5OB00984G

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