Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner-Meerwein Type 1,2-Amide Migration of 2-Spiropseudo-indoxyls

Niels Marien, Ting Luo, Guido Verniest

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Spiropseudoindoxyls were synthesized by using a gold(III)-catalyzed intramolecular nitroalkyne redox-dipolar cycloaddition cascade. These compounds were then transformed into novel piperidinone and azepanone fused indoles via a straightforward hydrogenation. The reaction mechanism of this ring expansion is believed to proceed through a rare Wagner-Meerwein type 1,2-amide migration.

Original languageEnglish
Article numberst-2016-b0779-l
Pages (from-to)934-938
Number of pages5
JournalSynlett
Volume28
Issue number8
DOIs
Publication statusPublished - 12 May 2017

Keywords

  • 1,2-acyl shift
  • dihydro-γ-carbolinone
  • indoles
  • spirocycles
  • Wagner-Meerwein

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