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
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.