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Issue 17, 2003
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Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines

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Abstract

2-(2- and 3-Pyridyl)anilines (1, 2), 2,2-dimethyl-N-[2-(2- and 3-pyridyl)phenyl]propanamides (3, 4), and 2-, 3- and 4-(2-methoxyphenyl)pyridines (7–9) are readily synthesized using cross-coupling reactions. Whereas the amines 1, 2 undergo side reactions, the corresponding amides 3, 4 are deprotonated with lithium 2,2,6,6-tetramethylpiperidide (LTMP): the compound 3 at C6′ under in situ quenching, and the compound 4 at C4′. When the ether 7 is subjected to the same reagent, lithiation occurs at C6′.

Graphical abstract: Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines

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Article information


Submitted
08 May 2003
Accepted
03 Jul 2003
First published
18 Jul 2003

Org. Biomol. Chem., 2003,1, 3064-3068
Article type
Paper

Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines

A. Rebstock, F. Mongin, F. Trécourt and G. Quéguiner, Org. Biomol. Chem., 2003, 1, 3064
DOI: 10.1039/B305043B

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