Reaction of Tröger's base analogues with Vilsmeier reagents

Qasim M. Malik, Andrew B. Mahon, Donald C. Craig, Andrew C. Try*

*Corresponding author for this work

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5 Citations (Scopus)

Abstract

As part of a program aimed at introducing functionality onto the Tröger's base framework post-synthesis, we investigated the formylation reaction of Tröger's base analogues with Vilsmeier reagents. We found that rather than the anticipated reaction at the aryl rings, these compounds react with Vilsmeier reagents to afford compounds with a modified strap, whereby the apical methylene group is replaced by a methylene strap bearing an N,N-disubstituted amine.

Original languageEnglish
Pages (from-to)8509-8514
Number of pages6
JournalTetrahedron
Volume67
Issue number44
DOIs
Publication statusPublished - 4 Nov 2011

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    Malik, Q. M., Mahon, A. B., Craig, D. C., & Try, A. C. (2011). Reaction of Tröger's base analogues with Vilsmeier reagents. Tetrahedron, 67(44), 8509-8514. https://doi.org/10.1016/j.tet.2011.08.095