Thiazole derivatives as potential chemotherapeutic agents: homolytic arylation of thiazole with phenylazotriphenylmethane.

The homolytic arylation of thiazole with phenylazotriphenylmethane (as a free radical source) was carried out to explore the potential chemotherapeutic activity of the resulting triphenylmethyl derivatives. The experimental data differed from similar results on other isosteric heterocycles: one compound only was obtained, having both phenyl and triphenylmethyl groups in the heterocyclic nucleus. The structure of 2-phenyl-5-triphenylmethylthiazole was established by IR, 1H-NMR, and mass spectroscopy. In particular, the mass spectral investigation indicated the cleavage of the 2,3- and 4,5-ring bonds, in contrast with the usual behavior of other thiazole derivatives with no triphenylmethyl substituent.