1: SOCl2 / CH2Cl2 3: NaOMe / methanol View Scheme

copper(l) iodide; 1,10-phenanthroline; caesium carbonate; ethanethiolic acid in 1,4-dioxane T=20 - 100°C; 13.25 h; Inert atmosphere;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; silica gel in acetonitrile 0.15 h; Irradiation;

pyridine; MeCH=CHCO2Et; nickel dichloride; zinc in methanol T=20°C; Inert atmosphere;

pyridine; [2,2']bipyridinyl; nickel dichloride; zinc in methanol T=20°C; 5 h; Inert atmosphere;

1.1: pyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.08 h / 0 °C / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 - 20 °C / |Inert atmosphere 2.2: 0.5 h / |Inert atmosphere 3.1: thiourea / ethanol / 4 h / 20 °C / |Inert atmosphere; |Reflux 3.2: 2 h / |Inert atmosphere; |Reflux 4.1: zinc; nickel dichloride; pyridine; MeCH=CHCO2Et / methanol / 20 °C / |Inert atmosphere View Scheme

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 - 20 °C / |Inert atmosphere 1.2: 0.5 h / |Inert atmosphere 2.1: thiourea / ethanol / 4 h / 20 °C / |Inert atmosphere; |Reflux 2.2: 2 h / |Inert atmosphere; |Reflux 3.1: zinc; nickel dichloride; pyridine; MeCH=CHCO2Et / methanol / 20 °C / |Inert atmosphere View Scheme

1.1: potassium hydroxide / ethanol; water / 3 h / |Reflux 2.1: potassium hydroxide / ethanol; dimethyl sulfoxide / 0.17 h / 20 °C 2.2: 15 h / 50 °C View Scheme

1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 20 °C 2: sodium sulfide hydrate; anhydrous iron chloride / N,N-dimethyl-formamide / 6 h / 120 °C / |Inert atmosphere View Scheme

sodium carbonate; trifluoroacetic anhydride 1) CH2Cl2, r.t., 1 h; Yield given. Multistep reaction;