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Organocatalytic multicomponent coupling to access a highly functionalised tetracyclic furoindoline: interrupted Passerini/Joullié-Ugi cascade reaction.

Takeshi YamadaSentaro Okamoto
Published in: Chemical communications (Cambridge, England) (2022)
The interrupted Passerini reaction of 3-(2-isocyanoethyl)-indole catalysed by 3,5,6-trifluoro-2-pyridone is described. The reaction diastereoselectively provided a tetracyclic furolindoline, which proved to be a good substrate for the Joullié-Ugi reaction; therefore, the sequential Passerini/Joullié-Ugi reactions were performed in one-pot to rapidly provide versatile and highly functionalised furoindolines from 3-(2-isocyanoethyl)-indole.
Keyphrases
  • electron transfer
  • room temperature
  • ionic liquid
  • structural basis