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Synthesis of Seven-Membered Azepino[3,2,1-hi]indoles via Rhodium-Catalyzed Regioselective C–H Activation/1,8-Diazabicyclo[5.4.0]undec-7-ene-Catalyzed Intramolecular Amidation of 7‑Phenylindoles in One Pot

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posted on 07.11.2019, 18:07 by Yumeng Yuan, Guoshuai Pan, Xiaofeng Zhang, Buhong Li, Shengchang Xiang, Qiufeng Huang
An unprecedented rhodium-catalyzed regioselective C–H activation/1,8-diazabicyclo[5.4.0]­undec-7-ene-catalyzed intramolecular amidation of 7-arylindoles with diazomalonates is described that provides a straightforward route to seven-membered azepino­[3,2,1-hi]­indoles in good to excellent yields in one pot. A wide range of functional groups, including F, OMe, NPh2, SiMe3, Cl, CN, CHO, COMe, CO2Me, CF3, and NO2, were all well-tolerated.

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