-碘代琥珀酰亚胺介导的苯并稠合双咪唑的合成：由氟化炔丙基脒的一锅串联反应实现
-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines.
作者信息
Li Shan, Lei Lu, Feng Bin, Liu Xiaofeng, Xian Liqing, Li Yajun
机构信息
Guangxi Key Laboratory of Urban Water Environment, Key laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, College of Chemistry and Environment Engineering, Baise University, 21 Zhongshan No.2 Road, Baise 533000, China.
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, China.
出版信息
J Org Chem. 2023 Apr 7;88(7):4101-4111. doi: 10.1021/acs.joc.2c02379. Epub 2023 Mar 16.
A -iodosuccinimide (NIS)-mediated divergent and efficient tandem reaction between fluorinated propargyl amidines and aromatic -diamines without any metal catalyst and additive under mild reaction conditions was developed for the synthesis of benzo-fused bisimidazoles in moderate to excellent yields. Preliminary mechanistic studies suggested that this reaction proceeded by an intermediate of secondary amine derived from 5-iodomethyl imidazole, and NIS played another role of oxidation reagent to promote the formation of a benzimidazole motif.
开发了一种由N-碘代琥珀酰亚胺（NIS）介导的、在温和反应条件下、无需任何金属催化剂和添加剂的氟化炔丙脒与芳香族二胺之间的发散且高效的串联反应，用于以中等至优异的产率合成苯并稠合双咪唑。初步机理研究表明，该反应通过5-碘甲基咪唑衍生的仲胺中间体进行，且NIS起到了促进苯并咪唑基序形成的氧化试剂的另一作用。
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