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

Troeger'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-hydr...

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Veröffentlicht in:Tetrahedron 2011-08, Vol.67 (32), p.5798-5805
Hauptverfasser: Malik, Qasim M, Ijaz, Sadia, Craig, Donald C, Try, Andrew C
Format: Artikel
Sprache:eng
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Zusammenfassung:Troeger'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 Troeger's base analogue.
ISSN:0040-4020
DOI:10.1016/j.tet.2011.05.128