Self-immolative base-mediated conjugate release from triazolylmethylcarbamates

Blencowe, C. A., Thornthwaite, D. W., Hayes, W. ORCID: https://orcid.org/0000-0003-0047-2991 and Russell, A. T. (2015) Self-immolative base-mediated conjugate release from triazolylmethylcarbamates. Organic and Biomolecular Chemistry, 13 (32). pp. 8703-8707. ISSN 1477-0520 doi: 10.1039/c5ob00984g

Abstract/Summary

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.