Syntheses of substituted 2-(1-methyl-2-imidazolyl)quinolines

Article abstract of DOI:10.1002/jhet.5570340526

Reaction of methyllithium with 1-methyl-2-imidazolecarboxaldehyde afforded the corresponding alcohol 2. Oxidation of compound 2 with manganese dioxide gave 2-acetyl-1-methylimidazole (3). Using compound 3 and substituted isatins 4, the corresponding quinoline-4-carboxylic acids (5) were prepared. The reaction of acid imidazolides of 5 with appropriate amines yielded the amides 6. Carbamic acid esters 10 ware prepared by the Curtius rearrangement in good yield. Substituted quinolin-4-amines 13 were obtained by the acid hydrolysis of compound 10 (R₁ = t-Bu). Alkylation of amines 13 with diakylaminoalkyl chlorides gave compounds 14.