Experimental and theoretical study of the reactivity of thiazole and 4,5-dimethylthiazole towards free phenyl and substituted phenyl radicals was written by Vitry-Raymond, Jacqueline;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1963.Synthetic Route of C9H7NS This article mentions the following:
The reactivity of thiazole (I) towards free phenyl and p-nitrophenyl radicals (obtained by the thermal decomposition of Bz2O2 and p-nitrophenyldiazonium salts, resp.) was investigated. The results are interpreted on the basis of the radical polarization energies calculated by the mol. orbital method. I and Bz2O2 in a molar ratio of 55:1 heated at 80° under N, excess I removed, the residue hydrolyzed, and the mixture steam distilled gave a mixture of 52% 2- (II), 37% 5- (III), and 11% 4-phenylthiazole (IV). The crude residue from a similar run extracted with C6H6, the extract successively reextracted with concentrated HCl and concentrated aqueous NaOH, the acidic extract neutralized and extracted with Et2O, and the extract evaporated yielded 8% mixture of 54-6% II, 29-31% III, and 13-17% IV; the alk. extract neutralized gave BzOH, m. 122°, and p-PhC6H4CO2H, m. 114°. These results show that the steam distillation apparently caused a reduction of the yields of IV and that in all runs the decreasing order of reactivity of the various positions in I was 2 > 5 > 4. The spectroscopic analysis of the steam-distilled product showed the presence of 60% II, 24% III, and 16% IV. I treated with p-nitrodiazonium salts under the conditions described previously for the reaction with 4,5-dimethylthiazole (CA 55, 22288c) gave 14% of a mixture of 3 isomeric monosubstitution products. The electron distribution in 2-, 4-, and 5-methylthiazole and in 4,5-dimethylthiazole was calculated In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).
5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Synthetic Route of C9H7NS
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica