State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210023, People's Republic of China.
Nanjing Foreign Language School , Nanjing 210008, People's Republic of China.
J Org Chem. 2017 Feb 3;82(3):1567-1574. doi: 10.1021/acs.joc.6b02760. Epub 2017 Jan 23.
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).
本文描述了一种基于新开发的 N-溴代琥珀酰亚胺（NBS）诱导的环化反应的方法，用于从含有吲哚单元的简单β-烯胺酯或β-烯胺酮制备三环氮杂[4,5-b]吲哚。提出了一种涉及Pictet-Spengler 环化、氮杂环丙烷形成和区域选择性 C-N 键断裂的反应机理，以解释中环的形成和吸电子基团（酯基、酮基）的迁移。
