An unprecedented base-promoted domino reaction of methyleneindolinones and N-tosyloxycarbamates for the construction of bispirooxindoles and spiroaziridine oxindoles

Chem Commun (Camb). 2015 Jul 7;51(53):10726-9. doi: 10.1039/c5cc03793j.

Abstract

An efficient and unprecedented domino reaction of methyleneindolinones and N-tosyloxycarbamates has been developed to afford structurally complex and diverse bispirooxindoles in excellent yields (up to 98%) and spiroaziridine oxindoles in moderate to good yields (55-91%). Moreover, this protocol could also provide the unsymmetrical bispirooxindoles and various fused spirocyclic pyrrolidines in excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aziridines / chemistry*
  • Crystallography, X-Ray
  • Indoles / chemistry*
  • Molecular Conformation
  • Oxindoles
  • Pyrrolidines / chemistry
  • Spiro Compounds / chemistry*

Substances

  • Aziridines
  • Indoles
  • Oxindoles
  • Pyrrolidines
  • Spiro Compounds
  • 2-oxindole
  • aziridine