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A DBU-catalyzed Michael-Pinner-isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif.

Yan-Shuo ZhuWen-Bo WangBei-Bei YuanYa-Ning LiQi-Lin WangZhan-Wei Bu
Published in: Organic & biomolecular chemistry (2018)
The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed, and the corresponding highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif were obtained in up to 92% yields. This protocol also provides an efficient method for the synthesis of an α-cyano-γ-butyrolactone bispirooxindole. In addition, a one-pot three-component cascade reaction was conducted. Also, the asymmetric version of the cascade reaction was achieved.
Keyphrases
  • molecular docking
  • room temperature
  • psychometric properties
  • molecular dynamics simulations
  • tandem mass spectrometry