2 H -Thiazolo[4,5- d ][1,2,3]triazole: synthesis, functionalization, and application in scaffold-hopping.

Autor: Miyazaki R; Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan junyamaguchi@waseda.jp., Takada F; Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan junyamaguchi@waseda.jp., Kikuchi T; Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan junyamaguchi@waseda.jp., Oguro Y; Takeda Pharmaceutical Company Limited 2-26-1 Muraoka-Higashi Fujisawa Kanagawa 251-8555 Japan., Kamata M; Takeda Pharmaceutical Company Limited 2-26-1 Muraoka-Higashi Fujisawa Kanagawa 251-8555 Japan., Yukawa T; Takeda Pharmaceutical Company Limited 2-26-1 Muraoka-Higashi Fujisawa Kanagawa 251-8555 Japan., Kato K; Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan junyamaguchi@waseda.jp., Muto K; Institute of Transformative Bio-molecules, Nagoya University Furo-cho, Chikusa Nagoya 464-8601 Japan muto.kei.v4@f.mail.nagoya-u.ac.jp., Yamaguchi J; Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan junyamaguchi@waseda.jp.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2024 Sep 03. Date of Electronic Publication: 2024 Sep 03.
DOI: 10.1039/d4sc03874f
Abstrakt: This manuscript unveils the synthesis of 2 H -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 S N Ar 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.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE