Aniline Dearomatization and Silver-Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2-cd]indoles from 2-Alkynylanilines and 2-Alkynylbenzaldoximes
Aniline Dearomatization and Silver-Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2-cd]indoles from 2-Alkynylanilines and 2-Alkynylbenzaldoximes
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苯胺脱芳构化和银催化 [3 3] 偶极环加成：从 2-炔基苯胺和 2-炔基苯甲醛肟高效构建 Oxocino[4,3,2-cd]吲哚
DOI：
10.1002/anie.201507277
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
Fan Renhua
中科院分区：
文献类型：
--
作者：
Han D;an;He Qiuqin;Fan Renhua
2‐炔基苯胺是吲哚合成中很有吸引力的原料，因为它们的易得性。本文报道了从2 -炔基苯胺和2 -炔基苯甲醛肟中高效构建多取代氧肟[4,3,2 - cd]吲哚的一锅逐步方法。该方法包括2‐炔基苯胺的氧化去芳构化，银催化与2‐炔基苯甲醛的[3+3]环加成，以及随后的热自由基骨架重排和芳构化。
2‐Alkynylanilines are attractive starting materials in indole synthesis because of their ready availability. Herein, a one‐pot stepwise procedure is reported for efficient construction of multisubstituted oxocino[4,3,2‐cd]indoles from 2‐alkynylanilines and 2‐alkynylbenzaldoximes. The method comprises the oxidative dearomatization of 2‐alkynylanilines, the silver‐catalyzed [3+3] cycloaddition with 2‐alkynylbenzaldoximes, and subsequent thermal radical skeletal rearrangement and aromatization.