Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement was written by Zambon, Alfonso;Borsato, Giuseppe;Brussolo, Stefania;Frascella, Pietrogiulio;Lucchini, Vittorio. And the article was included in Tetrahedron Letters in 2008.COA of Formula: C9H7NS This article mentions the following:
A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metalated thiazoles by tuning the reaction conditions. The proposed mechanism, based on exptl. evidence, is characterized by the catalytic role of thiazole bisadducts as metal-transfer agents. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: C9H7NS).
5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.COA of Formula: C9H7NS
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica