pyridine; malonic acid in water

bis-triphenylphosphine-palladium(II) chloride; potassium carbonate in N,N-dimethyl-formamide T=145 - 150°C; 6 h;

piperidine; pyridine T=85°C; 28 h; Reflux;

1.1: iodine; magnesium / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: piperidine; pyridine / 28 h / 85 °C / Reflux View Scheme

in trifluoroacetic acid

1.1: sulfuric acid / 72 h / 60 °C 2.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 2.2: 16 h / 0 - 25 °C 3.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme

1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: palladium diacetate / dichloromethane; diethyl ether / 1 h / 0 - 20 °C 4: lithium hydroxide hydrate / tetrahydrofuran / 0.5 h / 50 °C View Scheme

1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3.1: palladium diacetate / dichloromethane; diethyl ether / 1 h / 0 - 20 °C 4.1: lithium hydroxide hydrate / tetrahydrofuran / 0.5 h / 50 °C 5.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / Reflux 5.2: 16 h / Reflux 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C 7.1: hydrogenchloride / water; methanol / 3 h / 20 °C 7.2: pH 8 - 9 View Scheme

oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane T=0 - 20°C; 2 h;

thionyl chloride