Miyazaki Ryuya, Takada Fumito, Kikuchi Takunari, Oguro Yuya, Kamata Makoto, Yukawa Takafumi, Kato Kenta, Muto Kei, Yamaguchi Junichiro
Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan
Takeda Pharmaceutical Company Limited 2-26-1 Muraoka-Higashi Fujisawa Kanagawa 251-8555 Japan.
Chem Sci. 2024 Sep 3;15(38):15835-40. doi: 10.1039/d4sc03874f.
This manuscript unveils the synthesis of 2-thiazolo[4,5-][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 SAr 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.
本手稿揭示了2-噻唑并[4,5-][1,2,3]三唑（ThTz）的合成，这是一种前所未有的[5-5]稠合杂芳环体系，并建立了一种可扩展的合成方法，用于大量生产在噻唑环上带有砜基的ThTz环。砜部分被证明是一种通用的反应性标签，有助于进行多种转化，如亲核芳香取代反应、金属催化的偶联反应和基于自由基的烷基化反应。此外，三唑环的官能化突出了这种新开发的杂芳族化合物作为有价值的杂芳基构建块的潜力，促进了药物化学中的骨架跃迁策略。
