Intramolecular epoxide ring opening cyclisation reactions involving guanidines

Zainab Al-Shuhaib, Marcel Arndt, Mark Dennis, Daniel Evans, Iestyn Jones, Vera Leitmann, Patrick Murphy, Dion Roberts, Richard Rowles, Yones K. Sadaghiani, Andrew J. Thornhill, Robert J. Nash, Jackie Hollinshead, Barbara Bartholomew, Graham Tizzard, Simon Coles

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    Abstract

    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.
    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

    Keywords

    • guanidines
    • epoxides
    • epoxidation
    • DMDO
    • iodocyclisations
    • galactosidase inhibition

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