Synthesis and reactivity of dimethoxy-functionalised Tröger's base analogues

Qasim M. Malik, Sadia Ijaz, Donald C. Craig, Andrew C. Try*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    19 Citations (Scopus)

    Abstract

    Tröger's base analogues were prepared bearing methoxy groups in the 1,7-, 2,8-, 3,9- or 4,10-positions. These compounds were converted to their dihydroxy analogues in excellent yields upon treatment with boron tribromide and the 4,10-dihydroxy analogue could be prepared by directly from 4-hydroxyaniline. The synthetic utility of the dihydroxy-functionalised compounds as building blocks was demonstrated by the synthesis of a dialkoxy and a diester Tröger's base analogue.

    Original languageEnglish
    Pages (from-to)5798-5805
    Number of pages8
    JournalTetrahedron
    Volume67
    Issue number32
    DOIs
    Publication statusPublished - 12 Aug 2011

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