A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Alan M. Jones, Stephen Patterson, Magali Myriam Lorion, Alexandra Martha Zoya Slawin, Nicholas James Westwood

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.
Original languageEnglish
Pages (from-to)8998-9011
Number of pages14
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number38
Early online date30 Aug 2016
DOIs
Publication statusPublished - 14 Oct 2016

Keywords

  • Rearrangement
  • Medium-sized ring
  • Core-switching
  • Diversity-Oriented Synthesis
  • Pyrrolo[2,3-b]quinoline
  • Diazocino[1,2-a]indolinone

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