Radical dearomatising spirocyclisations onto the C-2 position of benzofuran and indole

Afua S. Kyei, Kirill Tchabanenko, Jack E. Baldwin, Robert M. Adlington

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

New spirolactams were obtained in radical dearomatising spirocyclisations of alkyl, vinyl and aryl radicals tethered at the C-2 positions of benzofuran and indole. Spirolactams were obtained via an intramolecular radical ipso-type spirocyclisation in benzofuran and indole systems. Alkyl, vinyl and aryl radicals, tethered at the C-2 position of the heterocycle underwent radical cyclisation to produce novel tricyclic partially dearomatised heterocycles in moderate yields. Fragmentation of the furan ring was observed subsequent to spirocyclisation of a vinyl radical onto a benzofuran.

Original languageEnglish
Pages (from-to)8931-8934
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number48
DOIs
Publication statusPublished - 22 Nov 2004
Externally publishedYes

Keywords

  • Alkyl radical
  • Aryl radical
  • Benzofuran
  • Indole
  • Spirocycle
  • Spirocyclisation
  • Vinyl radical

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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