Versatile pyrolytic synthesis of fused polycyclic heteroaromatic compounds

R Alan Aitken, Alasdair N. Garnett

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Thirty-six new stabilised phosphonium ylides designed to undergo thermal loss of Ph3PO and radical domino cyclisation have been prepared and are generally found to undergo the desired reaction under flash vacuum pyrolysis conditions at 850 °C. A wide range of tetra- and penta-cyclic fused ring heterocycles, many previously unknown, are thus formed in moderate to high yield in a single step. By using suitably substituted starting materials, substituents such as CH3 and Cl can be installed at various positions in the products. The method has also been demonstrated in a combinatorial mode to generate a small library of twelve fused ring heterocycles in a single pyrolysis.
Original languageEnglish
Pages (from-to)4955-4977
Number of pages23
JournalSynthesis
Volume49
Issue number22
Early online date11 Oct 2017
DOIs
Publication statusPublished - Nov 2017

Keywords

  • Cyclization
  • Domino reaction
  • Fused-ring systems
  • Gas-phase reaction
  • Heterocycles
  • Radical reaction
  • Ylides

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