Thermal Rearrangement of Indolyl Oxime Esters to Pyridoindoles

Fernando Portela Cubillo, Brian Andrew Surgenor, R Alan Aitken, John Christopher Walton

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

Acyl oximes derived from a variety of indolylalkanones underwent a ring closure sequence during FVP to afford 9H-pyrido[2,3-b]indoles. Unlike UV light promoted reactions of oxime esters, the mechanism is almost certainly not mediated by iminyl radicals but probably involves tautomerism, elimination of acetic acid, and a final electrocyclic ring closure.

Original languageEnglish
Pages (from-to)8124-8127
Number of pages4
JournalThe Journal of Organic Chemistry
Volume73
Issue number20
DOIs
Publication statusPublished - 17 Oct 2008

Keywords

  • O-PHENYL OXIMES
  • FORMAL SYNTHESIS
  • IMINYL RADICALS
  • ALDOXIME ESTERS
  • PEROXIDE
  • DECOMPOSITION
  • DERIVATIVES
  • EPR

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