bis(trimethyl-silyl)-trifluoroacetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane 20 deg C, 4 h. then 110 deg C, 18 h.;

1: With potassium tert-butylate in N,N-dimethyl-formamide T=-15°C; 1.33333 h; 2: With water in N,N-dimethyl-formamide T=50°C; 2 h;

hydrogenchloride; bunazosin in 1,4-dioxane; dichloromethane; acetonitrile

hydrogenchloride; bunazosin in 1,4-dioxane; acetonitrile

1: With sulfuric acid T=20 - 30°C; 3 h; 2: With water T=0 - 5°C; 1.5 h; Product distribution / selectivity;

potassium hydroxide in methanol 4 h; Heating; Title compound not separated from byproducts;

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; N,N-bis(trimethylsilyl)-trifluoroacetamide / toluene / 12 h / 25 - 110 °C / Inert atmosphere 2.1: sulfuric acid / 3 h / 20 - 30 °C 2.2: 1.5 h / 0 - 5 °C View Scheme

1.1: potassium carbonate; sodium periodate; potassium permanganate / tert-butyl alcohol; water / 1 h / 50 °C 2.1: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / |Inert atmosphere 3.1: ammonium acetate / tetrahydrofuran / 1 h / |Reflux; |Inert atmosphere 4.1: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 5.1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 6.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 7.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 8.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 8.2: 2 h / -10 - 0 °C 9.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 9.2: 2 h / 50 °C View Scheme

1.1: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / |Inert atmosphere 2.1: ammonium acetate / tetrahydrofuran / 1 h / |Reflux; |Inert atmosphere 3.1: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 4.1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 5.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 6.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 7.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 7.2: 2 h / -10 - 0 °C 8.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 8.2: 2 h / 50 °C View Scheme

1.1: ammonium acetate / tetrahydrofuran / 1 h / |Reflux; |Inert atmosphere 2.1: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 3.1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 4.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 5.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 6.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 6.2: 2 h / -10 - 0 °C 7.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 7.2: 2 h / 50 °C View Scheme