4.8 Article

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles

Journal

ORGANIC LETTERS
Volume 19, Issue 17, Pages 4476-4479

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01957

Keywords

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Funding

  1. National Basic Research Program of China [(973)-2015CB856603]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  3. National Natural Science Foundation of China [20472096, 21372241, 21572052, 20672127, 21421091, 21372250, 21121062, 21302203, 21772037, 20732008]

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An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c] dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.

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