Details

Autor(en) / Beteiligte

• Zhao, Jinwu
• Xiao, Qiannan
• Chen, Jiaxi
• Xu, Jingxiu

Titel

Metal‐Free Synthesis of Imidazothiazoles from Thioimidazoles and Ketones Mediated by Selectfluor

Ist Teil von

• European journal of organic chemistry, 2020-08, Vol.2020 (32), p.5201-5206

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• This paper presents a practical and efficient strategy for the preparation of imidazol[2,1‐b]‐thiazoles from thioimidazoles and ketones mediated by Selectfluor. The proposed mechanism suggests that this transformation took place through electrophilic thiolation at an α‐carbon of ketones by sulfur cation, which is produced by the oxidation of thioimidazole by Selectfluor. This metal‐free protocol tolerated various ketones, including methyl ketones or non‐methyl ketones, aryl ketones or aliphatic ketones. The experimental results indicated that steric hindrance of the substituents at the α‐position of ketones or on the aromatic ring of aryl ketones had significant influence on the yields of imidazol[2,1‐b]‐thiazoles. Thioimidazole and benzothioimidazoles were well tolerated while 5‐substituted benzothioimidazoles provided the mixture of the corresponding 6‐substituted and 7‐substituted benzoimidazo[2,1‐b]thiazole products.