Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
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碘(III)试剂介导的2-烯基苯胺分子内胺化制备吲哚
DOI：
10.1002/adsc.201701551
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发表时间：
2018
影响因子：
5.4
通讯作者：
Mo Dong-Liang
中科院分区：
文献类型：
--
作者：
Zhao Chun-Yang;Li Kun;Pang Yu;Li Jia-Qing;Liang Cui;Su Gui-Fa;Mo Dong-Liang
在易得的碘（III）试剂的作用下，通过2-烯基苯胺的分子内胺化反应，在较短的反应时间内以较高的产率高效合成了多种3-取代和2，3-二取代吲哚。机理研究表明，反应途径通过氮鎓离子，3-乙酰氧基吲哚啉是吲哚形成的关键中间体。吲哚产物易于在克级规模上制备，并且在mCPBA存在下使用催化3，5-二甲基苯基碘也顺利进行胺化。此外，吲哚并[3，2-a]咔唑支架以良好的产率在六个步骤中从商业邻碘苯胺制备。
A variety of 3‐substituted and 2,3‐disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2‐alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3‐acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5‐dimethylphenyl iodine in the presence ofmCPBA. Furthermore, the indolo[3,2‐a]carbazole scaffold was prepared in good yield in six steps from commercialortho‐iodoaniline.