Application of organolithium and related reagents in synthesis. Part 14. Synthetic strategies based on aromatic metallation. A concise regiospecific conversion of benzoic acids into their ortho-pyridoyl derivatives

✍ Scribed by Jan Epsztajn; Andrzej Jóźwiak; Jerzy A. Krysiak

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 628 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)87002-2

✦ Synopsis

Dedicated with admiration and a]j'ktion, to Alan R. Katritzky on his 63th birthday Absbod: The synthesis o/the 3-hy~~-3-~ri~l-isotndolin-l-onEs (5) and (6) via metallation (n-BuLt) of the benzanilides (I), and then the reaction of the generated bis lithinted anilides (2) with N,N-dimet&lamides or methyl esters of pyridinecarboxylic acids fbensoylation reagents), and subsequent acidic hydrolysis of (5) and (6) as a way (general synthettc strategy) of regiospecijlc transformation of benzoic acids into their ortho-benzoylated derivatives, is described.