2H-Thiazolo[4,5-d][1,2,3]triazole: Synthesis, Functionalization, and Application in Scaffold-Hopping
Miyazaki, R.; Takada, F.; Kikuchi, T.; Oguro, Y.; Kamata, M.; Yukawa, T.; Kato, K.; Muto, K.; Yamaguchi, J.
Chem. Sci. 2024. Advanced Article.
DOI: 10.1039/D4SC03874F
This manuscript unveils the synthesis of 2H-thiazolo[4,5-d][1,2,3]triazole (ThTz), an unprecedented [5-5]-fused heteroaromatic system, and established a scalable synthetic procedure for producing large quantities of the ThTz ring bearing a sulfone group on the thiazole ring. The sulfone moiety proves to be a versatile reactive tag, facilitating diverse transformations such as SNAr reactions, metal-catalyzed couplings, and radical-based alkylations. Furthermore, functionalization of the triazole ring highlights the potential of this newly developed heteroaromatic compound as a valuable heteroaryl building block, promoting scaffold hopping strategies in medicinal chemistry.
