Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of <i>O</i>-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines
Sitian Yuan, Xuan Liu, Zhongzhi Huang, Shuanggen Gui, Yuexing Diao, Yiyuan Peng, Qiuping Ding
Abstract
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.
Topics & Concepts
TrifluoromethylationChemistryReagentTrifluoromethylCascadeCombinatorial chemistryChlorideOrganic chemistryChromatographyAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesSynthesis and Biological Evaluation