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

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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 ( IF 3.3 ) Pub Date : 2022-12-01 , DOI: 10.1021/acs.joc.2c02100
Sitian Yuan ₁ , Xuan Liu ₁ , Zhongzhi Huang ₁ , Shuanggen Gui ₁ , Yuexing Diao ₁ , Yi-Yuan Peng ₁ , Qiuping Ding ₁

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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.

中文翻译：

四丁基氯化铵诱导的 O-异氰基二芳基胺的级联自由基加成/环化：一种合成 11-三氟甲基化二苯二氮卓类化合物的新方案

使用 Togni 试剂作为三氟甲基源，通过 TBAC 诱导的邻异氰基二芳基胺的三氟甲基化/环化，开发了一种用于合成 11-三氟甲基化二苯并二氮杂卓的简单方案。这是关于一步构建含 CF ₃二苯二氮卓类药物骨架的第一份报告。此外，在无过渡金属的条件下，还得到了一系列 11-三氟甲基化二苯并二氮杂卓，收率中等至极佳。

更新日期：2022-12-01

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