Azepinoindole Synthesis via a N-Bromosuccinimide-Induced Cycloisomerization of Enaminoester/Enaminone

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• 作者：Lina Chang ; Tao Guo ; Ziyi Wang ; Shaozhong WangZhu-Jun Yao
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：82
• 期：3
• 页码：1567-1574
• 全文大小：455K
• ISSN：1520-6904

文摘

A protocol based on a newly developed N-bromosuccinimide (NBS)-induced cycloisomerization was described to prepare tricyclic azepino[4,5-b]indoles from simple β-enaminoesters or β-enaminones containing an indole unit. A mechanism involving a Pictet–Spengler cyclization, an aziridine ring formation, and a regioselective C–N bond cleavage was proposed to account for the medium-sized ring formation and the migration of electron-withdrawing group (ester, ketone).