Reaction of Tröger's base analogues with Vilsmeier reagents

Qasim M. Malik; Andrew B. Mahon; Donald C. Craig; Andrew C. Try

doi:10.1016/j.tet.2011.08.095

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	8509-8514
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2011.08.095
Publication status	Published - 4 Nov 2011

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10.1016/j.tet.2011.08.095

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abstract = "As part of a program aimed at introducing functionality onto the Tr{\"o}ger's base framework post-synthesis, we investigated the formylation reaction of Tr{\"o}ger'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.",

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AU - Malik, Qasim M.

AU - Mahon, Andrew B.

AU - Craig, Donald C.

AU - Try, Andrew C.

PY - 2011/11/4

Y1 - 2011/11/4

N2 - 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.

AB - 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.

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DO - 10.1016/j.tet.2011.08.095

M3 - Article

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VL - 67

SP - 8509

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Reaction of Tröger's base analogues with Vilsmeier reagents

Abstract

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