Login / Signup

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine via isocyanide-based multicomponent reaction.

Xiu-Yu ChenYing HanJing SunChao-Guo Yan
Published in: Beilstein journal of organic chemistry (2024)
An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)cyclopenta-1,3-dienes from addition of alkyl isocyanide to two molecules of but-2-ynedioates and sequential formal [3 + 2] cycloaddition reaction with 5,6-unsubstituted 1,4-dihydropyridine.
Keyphrases
  • ionic liquid
  • randomized controlled trial
  • electron transfer
  • quantum dots
  • reduced graphene oxide
  • sensitive detection
  • high density