Competition between cyclisation and bisimine formation in the reaction of 1,3-diaminopropanes with aromatic aldehydes

Julie Myree Locke, Renate Griffith, Trevor D. Bailey, Robyn L. Crumbie

    Research output: Contribution to journalArticle

    35 Citations (Scopus)

    Abstract

    Condensation of 1,3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1,3-diaminopropane or 1,3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring of the aldehyde. Calculations indicate that the electronic nature of this aryl ring substituent influences both the relative thermodynamic stability of the final products and the reactivity of the aldehyde as an electrophile.
    Original languageEnglish
    Pages (from-to)10685-10692
    Number of pages8
    JournalTetrahedron
    Volume65
    Issue number51
    Publication statusPublished - 2009

    Keywords

    • aldehydes
    • hexahydropyrimidine
    • imines
    • ketones
    • molecular orbitals
    • ring formation (chemistry)

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