Issue 22, 1998

Quaternization at the picolinic carbon. Application to the synthesis of pyridylalkanecarboxylic acids

Abstract

The paper describes two different methodologies for the construction of a quaternary center at the picolinic site, and their application to the synthesis of pyridylalkanecarboxylic acids. The first one involves a one-pot acetylation–Michael addition procedure followed by an alkylative quaternization of the picolinic carbon. The second one is based on the deprotonation at the picolinic carbon of 2-(α,α-dialkyl)pyridines using the superbasic mixture BuLi–diisopropylamine–ButOK (“KDA”). Both routes give very good yields.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 3807-3812

Quaternization at the picolinic carbon. Application to the synthesis of pyridylalkanecarboxylic acids

E. Pasquinet, P. Rocca, A. Godard, F. Marsais and G. Quéguiner, J. Chem. Soc., Perkin Trans. 1, 1998, 3807 DOI: 10.1039/A805778H

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