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

Research output: Contribution to journalArticle

Authors

  • Stephen Patterson
  • Magali M Lorion
  • Alexandra M Z Slawin
  • Nicholas J Westwood
  • Alan M Jones

Colleges, School and Institutes

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.

Details

Original languageEnglish
Pages (from-to)8998-9011
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number38
Early online date30 Aug 2016
Publication statusPublished - 14 Oct 2016