Anionic N-Fries rearrangement of N-alkyl-2-iodo anilides induced by iodine-magnesium exchange: Application for synthesis of strained 1,2,3-trisubstituted indoles
Anionic N-Fries rearrangement of N-alkyl-2-iodo anilides induced by iodine-magnesium exchange: Application for synthesis of strained 1,2,3-trisubstituted indoles
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DOI：
10.1021/ol7029905
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发表时间：
2008-03-20
期刊：
影响因子：
5.2
通讯作者：
Senanayake, Chris H.
中科院分区：
文献类型：
--
作者：
Ding, Fei;Zhang, Yongda;Senanayake, Chris H.
一种上级，温和，高产率的一锅法快速获得氧代苯胺已开发，涉及三个级联反应：碘镁交换，区域特异性邻N-Fries重排，并在原位捕获形成的苯胺阴离子。再加上McMurry环化，两步过程允许区域选择性地快速合成应变的1，2，3-三取代吲哚。
A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively.