Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines.

Sitian Yuan, Xuan Liu, Zhongzhi Huang, Shuanggen Gui, Yuexing Diao, Yi-Yuan Peng, Qiuping Ding

The Journal of organic chemistry 2022 Dec 16

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A straightforward protocol for the synthesis of 11-trifluoromethylated dibenzodiazepines has been developed via TBAC-induced trifluoromethylation/cyclization of o-isocyanodiaryl amines using Togni's reagent as the trifluoromethyl source. This is the first report on the one-step construction of CF3-containing dibenzodiazepine drug skeletons. Additionally, a series of 11-trifluoromethylated dibenzodiazepines were afforded in moderate to excellent yields under transition-metal-free conditions.

Citation

Sitian Yuan, Xuan Liu, Zhongzhi Huang, Shuanggen Gui, Yuexing Diao, Yi-Yuan Peng, Qiuping Ding. Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines. The Journal of organic chemistry. 2022 Dec 16;87(24):16542-16549