Punna Shiva Kumar, Arockiaraj Mariyaraj, Rajeshkumar Venkatachalam
Organic Synthesis & Catalysis Lab, Department of Chemistry, National Institute of Technology Warangal, Hanumakonda-506004, Telangana, India.
Org Biomol Chem. 2024 Sep 18;22(36):7478-7484. doi: 10.1039/d4ob01221f.
A metal-free, iodine-catalyzed protocol has been developed for constructing biologically significant 5-aroyl 1,2,4-oxadiazole scaffolds using aryl methyl ketones and amidoximes. The strategy produces structurally diverse 5-aroyl 1,2,4-oxadiazoles in good to excellent yields, with a broad substrate scope that includes drug derived substrates. The reaction proceeds through iodine/DMSO-mediated oxidation of aryl methyl ketones, followed by imine formation and subsequent cyclization to yield the desired products. Additionally, this protocol has successfully produced the carbonyl analogs of ataluren and tioxazafen and has facilitated some intriguing late-stage transformations.
已开发出一种无金属、碘催化的方法，用于使用芳基甲基酮和偕胺肟构建具有生物学意义的5-芳酰基-1,2,4-恶二唑支架。该策略以良好至优异的产率生成结构多样的5-芳酰基-1,2,4-恶二唑，底物范围广泛，包括药物衍生的底物。反应通过碘/二甲亚砜介导的芳基甲基酮氧化，随后形成亚胺并随后环化以产生所需产物。此外，该方法已成功制备了阿他芦伦和噻唑嗪的羰基类似物，并促进了一些有趣的后期转化。
