1: 1,2,3-trimethoxyacridin-9(10H)-one With sodium hydride in tetrahydrofuran; mineral oil T=0°C; Inert atmosphere; 2: methyl iodide in tetrahydrofuran; mineral oil T=20°C; 2 h; Inert atmosphere;

potassium carbonate in acetone 2 h; Heating;

1: 75 percent / nitric acid / 0.17 h / 0 °C 2: 83 percent / hydrogen / platinum oxide / ethanol / 0.5 h / 2068.6 Torr 3: 92 percent / sodium hydroxide / toluene / 0 °C 4: 1.) sodium hydride / 1.) dimethylacetamide, 2.) room temperature, 3 h 5: 49 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 30 min, 3.) RT, 90 min 6: 55 percent / palladium-on-charcoal / xylene / 2 h / Heating View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere View Scheme

1: 6.5 percent / m-chloroperbenzoic acid (MCPBA), phosphate buffer (pH 8.0) / CH2Cl2 2: 85 percent / K2CO3 / acetone / 2 h / Heating View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere View Scheme

1.1: Eaton's reagent / 0.83 h / 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere View Scheme

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux 2.1: Eaton's reagent / 0.83 h / 80 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / 0 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / |Inert atmosphere 2.2: 1 h / 20 °C / |Inert atmosphere 3.1: sulfuric acid / butan-1-ol / 24 h / |Reflux 4.1: [2,2']bipyridinyl; copper(l) iodide; oxygen / N,N-dimethyl acetamide / 12 h / 160 °C / |Sealed tube View Scheme