2-(4-Aminophenyl)benzothiazoles related to 1 are potentially important pharmaceuticals. Metabolism apparently involves oxidation and esterification to 3. In water, hydrolysis and photolysis of 3 generates the nitrenium ion 4 that can be detected indirectly by N3- trapping and directly by UV-vis spectroscopy following laser flash photolysis. The transient, with λmax 570 nm, and a lifetime of 530 ns, reacts with N 3- at a diffusioncontrolled rate and generates the quinol 6 by reaction with water.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry