Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition

Rifahath M. Neyyappadath, Mark D. Greenhalgh, David Bradford Cordes, Alexandra M. Z. Slawin, Andrew D. Smith

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A serendipitously-discovered process for the synthesis of heterocyclic products containing a novel fused indoline-cyclobutanone ring system is reported. This process is believed to take place through in situ generation of a ketene intermediate, followed by intramolecular [2+2] cycloaddition with a pendant enamide. The formation of a ketene intermediate in this process is significant as the reaction conditions employed are analogous to those commonly used in tertiary amine Lewis base catalysis, where the potential intermediacy of ketenes is an important consideration that is often overlooked.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
VolumeEarly View
Early online date12 Apr 2019
Publication statusE-pub ahead of print - 12 Apr 2019


  • Lewis base catalysis
  • Ketene
  • [2+2]-cycloaddition
  • N-heterocycles
  • Indoline-cyclobutanone


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