Investigation of cationic Claisen-type electrophilic rearrangements of amides

Mohan Padmanaban, Luisa C. R. Carvalho, Desislava Petkova, Ji-Woong Lee, A. Sofia Santos, Maria Manuel Martinho Sequeira Barata Marques, Nuno Maulide

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Herein we report an extension of the electrophilic rearrangement of amides to the preparation of a, prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. (C) 2015 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)5994-6005
Number of pages12
JournalTetrahedron
Volume71
Issue number35
DOIs
Publication statusPublished - 2 Sep 2015

Keywords

  • oxa and aza-Claisen
  • Amides
  • Rearrangement
  • Hydrocoumarin
  • Isoquinolinone
  • ECHINULIN-TYPE COMPOUNDS
  • MODEL REACTION
  • 3-ALKYL-1-ALLYLINDOLES
  • DERIVATIVES
  • BIOGENESIS
  • ACYLATION
  • INDOLES
  • OLEFINS
  • SALTS

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