Intramolecular epoxide ring opening cyclisation reactions involving guanidines

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  • Zainab Al-Shuhaib
  • Marcel Arndt
    School of Chemistry, Bangor University
  • Mark Dennis
  • Daniel Evans
  • Iestyn Jones
  • Vera Leitmann
    School of Chemistry, Bangor University
  • Patrick Murphy
  • Dion Roberts
    School of Chemistry, Bangor University
  • Richard Rowles
  • Yones K. Sadaghiani
    School of Chemistry, Bangor University
  • Andrew J. Thornhill
    School of Chemistry, Bangor University
  • Robert J. Nash
    PhytoQuest Limited, Aberystwyth
  • Jackie Hollinshead
    PhytoQuest Limited, Aberystwyth
  • Barbara Bartholomew
    PhytoQuest Limited, Aberystwyth
  • Graham Tizzard
    University of Southampton
  • Simon Coles
    University of Southampton
The cyclisation of N-allyl- and N-homoallylguanidines using DMDO leading to the formation of novel 5- and 6-membered guanidine heterocycles is reported. Several of the products formed displayed weak inhibition of glycosidase enzymes.

Keywords

  • guanidines, epoxides, epoxidation, DMDO, iodocyclisations, galactosidase inhibition
Original languageEnglish
Pages (from-to)845-852
Number of pages8
JournalTetrahedron
Volume73
Issue number7
Early online date27 Dec 2016
DOIs
Publication statusPublished - 16 Feb 2017

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