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Superbase-promoted selective carbon-carbon bond cleavage driven by aromatization.

Can LiuXianjin ZhuYongzhen HanHaijun YangChangjin ZhuHua Fu
Published in: Organic & biomolecular chemistry (2019)
A novel selective carbon-carbon single bond cleavage has been disclosed through the copper-catalyzed reaction of 1-alkyl-3-alkylindolin-2-imine hydrochlorides with substituted 1-(bromomethyl)-2-iodobenzenes leading to fused N-heterocycles. Mechanistic studies showed that the intrinsic drive of aromatization and the action of the superbase derived from sodium tert-butoxide and dimethylsulfoxide were the key factors leading to the carbon-carbon single bond cleavage. Furthermore, the obtained N-heterocycles are indoloquinoline derivatives with wide biological activities.
Keyphrases
  • dna binding
  • transcription factor