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

Article abstract of DOI:10.1016/S0040-4020(01)87002-2

The synthesis of the 3-hydroxy-3-pyridyl-isoindolin-1-ones (5) and (6) via metallation (n-BuLi) of the benzanilides (1), and then the reaction of the generated bis lithiated anilides (2) with N,N-dimethylamides or methyl esters of pyridinecarboxylic acids (benzoylation reagents), and subsequent acidic hydrolysis of (5) and (6) as a way (general synthetic strategy) of regiospecific transformation of benzoic acids into their ortho-benzoylated derivatives, is described.