ChemInform Abstract: Quaternization at the Picolinic Carbon. Application to the Synthesis of Pyridylalkanecarboxylic Acids.

✍ Scribed by Eric Pasquinet; Patrick Rocca; Alain Godard; Francis Marsais; Guy Queguiner

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199916143

✦ Synopsis

Quaternization at the Picolinic Carbon. Application to the Synthesis of Pyridylalkanecarboxylic Acids. -Two different methods are applied to construct the quaternary center of title acids such as (V) and (VIII). The first is based on the deprotonation at the picolinic carbon of 2-(α,α-dialkyl)pyridines using the superbasic mixture. The second route involves the one-pot acetylation/cyanoethylation procedure to yield ketonitrile (XII) followed by an quaternization of the picolinic carbon with alkyl halides. Both routes give very good yields.