Heterocyclen aus o-Aminoketonen. XXIII [1]. Umsetzung von o-Aminoketonen mit Dicarbonsäuren

Heterocyclic Compounds from 2-Aminoketones. XXIII. Reaction of o-Aminoketones with Dicarboxylic Acids Saturated aliphatic dicarboxylic acids (C₄ C₇ and C₁₀) react with 2-aminobenzophenones in polyphosphoric acid (PPA) to form substituted derivatives of partial hydrogenated benzo[b][1,8]naphthyridines 2a–d and 2-anilino-quinoline-3-alkanoic-acids 5a–h . The heterologous derivatives of glutaric acid — containing S or N instead of β-CH₂ — with aminoketon undergo ring closure to give thiazino- and oxazino[3,2-b]quinolines 2e–h . Aromatic o-dicarboxylic acids with a –CH₂ CO- group react with aminoketones to yield anilinosubstituted 5i or pyrano[b]-condensed quinolines 6 . N,N′-Di-(2-benzoylphenyl)-dicarboxylicacid-diamides 3 with ammonia undergo cyclisation to α,ω-di-(4′phenyl-quinazolinyl-(2′))-alkanes 4 .