Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

F Aldabbagh, W R Bowman, E Mann, A M Z Slawin

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.

Original languageEnglish
Pages (from-to)8111-8128
Number of pages18
JournalTetrahedron
Volume55
Issue number26
Publication statusPublished - 25 Jun 1999

Keywords

  • SUBSTITUTION SRN1 REACTIONS
  • ADDITION-REACTIONS
  • 1,2-FUSED INDOLES
  • BUTYLTIN HYDRIDE
  • PYRIDINIUM RINGS
  • CYCLIZATION
  • ROUTE
  • ALKYLATIONS
  • ALKALOIDS
  • SULFIDES

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