Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.
Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.
复制标题
DOI：
10.1002/chem.202301141
复制
发表时间：
2023-04
期刊：
影响因子：
--
通讯作者：
Carmen Margaret White;Naranchimeg Zorigt;Tianning Deng;T. Driver
中科院分区：
文献类型：
--
作者：
Carmen Margaret White;Naranchimeg Zorigt;Tianning Deng;T. Driver
报道了一种有效的方法，该方法使用碘酰苯或双（三氟乙酰氧基）碘苯从2-取代苯胺制备具有生物活性的中等尺寸的N-杂环支架。可以改变磺酰胺和芳基之间的系链以获得二氢吖啶-、二苯并氮杂卓-或二苯并氮杂辛因支架。虽然在苯胺部分上的取代限于电子中性或缺电子基团，但在邻位取代基上容许更宽范围的官能团，并且可以实现位点选择性C-NAr键形成。初步的机理研究表明，中环的形成发生通过自由基反应中间体。
The development of an efficient process that produces bioactive medium-sized N-heterocyclic scaffolds from 2-substituted anilines using either iodosobenzene or (bis(trifluoroacetoxy)iodobenzene is reported. The tether between the sulfonamide and the aryl group can be varied to access dihydroacridine-, dibenzazepine-, or dibenzazocine scaffolds. While substitution on the aniline portion is limited to electron-neutral- or electron-poor groups, a broader range of functional groups are tolerated on the ortho-substituent and site selective C-NAr bond formation can be achieved. Preliminary mechanistic investigations suggest that medium-ring formation occurs via radical reactive intermediates.