Access to densely functionalized spirocyclopentenonyl oxindole frameworks via aza- and carbo-Piancatelli rearrangement

Org Biomol Chem. 2022 Jul 6;20(26):5249-5253. doi: 10.1039/d2ob00883a.

Abstract

A new strategy for access to spirocyclopentenonyl oxindole frameworks is disclosed. Suitably anchored furfuryl alcohol at C3 of an oxindole was used for the aza-Piancatelli rearrangement, which furnished spirocyclic aminocyclopentenone frameworks with catalytic phosphomolybdic acid. The scope of the transformation was extended to the carbo-Piancatelli rearrangement with various indole derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Charcoal*
  • Oxindoles
  • Stereoisomerism

Substances

  • Oxindoles
  • Charcoal