Application of Organolithium and Related Reagents in Synthesis. Part 23: Synthetic Strategies Based on ortho-Aromatic Metallation. Synthesis of 4b-Arylisoindolo[2,1-a]quinoline derivatives

The synthesis of the 2-aryl-3-hydroxyisoindol-1-ones 3 and their successive conversion via the reaction with 1-methoxy-1-trimethylsilyloxyethene in the presence of titanium(IV) chloride into 3-carboxymethylphthalimides 7 and subsequent cyclization via sequential treatment with oxalyl chloride and aluminium chloride as a way of regiospecific transformation of the benzenecarbocylic acids into the corresponding isoindolo[2,1-a]quinoline-5,11-diones 5 is described.