4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 22, Pages 14701-14711

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02289

Keywords

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Funding

  1. NSFC [21872028, 61520106015]
  2. Natural Science Foundation of Fujian Province [2017J01572]
  3. Foundation of Fujian Educational Committee [JZ160424]
  4. Fujian Province University Fund for New Century Excellent Talents

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An unprecedented rhodium-catalyzed regioselective C-H activation/1,8-diazabicyclo[5.4.0]undec-7-enecatalyzed 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, CO2 Me, CF3, and NO2, were all well-tolerated.

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