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.
D001391:Azo Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D005609:Free Radicals; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013844:Thiazoles / Q000138:chemical synthesis*; D014320:Triphenylmethyl Compounds / Q000138:chemical synthesis*
D001391:Azo Compounds; D005609:Free Radicals; D013844:Thiazoles; D014320:Triphenylmethyl Compounds