4.7 Article

Synthesis of benzo[a]carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Journal

CHEMICAL COMMUNICATIONS
Volume 52, Issue 50, Pages 7870-7873

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc03124b

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Funding

  1. Ministry of Science and Technology of the Republic of China [MOST 103-2113-M-003-008-MY3]
  2. National Taiwan Normal University [103-07-C]
  3. Instrumentation Centre at National Taiwan Normal University

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The dual character of benzoquinone is exploited for the synthesis of benzo[a]carbazole derivatives starting from 3-ethylindole derivatives. A diene is generated in situ from the 3-ethylindole derivative with the help of benzoquinone, where it acts as an oxidizing agent. Later it serves as a dienophile and participates in a Diels-Alder reaction with the diene to afford benzo[a]carbazole derivatives.

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