1: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.5 h; 2: methyl iodide in N,N-dimethyl-formamide T=0 - 20°C;

in N-methyl-acetamide

1: 53 percent / Copper bronze, K2CO3 / I2 / 24 h / 120 °C 2: Hydrazine hydrate (98percent) / Raney Ni / aq. ethanol / 1 h / Heating 3: 94 percent / 1.) aqueous NaNO2 / acetic acid; H2O / 1.) 0 deg C, 2.) 2 h, 0 deg C bis room temp. 4: 62 percent / acetone; methanol / 500 °C View Scheme

1: 53 percent / Copper bronze, K2CO3 / I2 / 24 h / 120 °C 2: Hydrazine hydrate (98percent) / Raney Ni / aq. ethanol / 1 h / Heating 3: 94 percent / 1.) aqueous NaNO2 / acetic acid; H2O / 1.) 0 deg C, 2.) 2 h, 0 deg C bis room temp. 4: 62 percent / acetone; methanol / 500 °C View Scheme

in 1,3,5-trimethyl-benzene 5 h; Heating;

1.1: potassium hydroxide / H2O / 5 h / Heating 1.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 2.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 3.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 4.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 5.1: ozone / methanol; CH2Cl2 / -78 °C 5.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 6.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 7.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 7.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 7.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 8.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 9.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 2.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 3.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4.1: ozone / methanol; CH2Cl2 / -78 °C 4.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 5.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 6.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 6.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 6.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 7.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 8.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 2.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3.1: ozone / methanol; CH2Cl2 / -78 °C 3.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 4.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 5.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 5.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 5.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 6.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 7.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 2.1: ozone / methanol; CH2Cl2 / -78 °C 2.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 3.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 4.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 4.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 4.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 5.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 6.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: ozone / methanol; CH2Cl2 / -78 °C 1.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 2.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 3.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 3.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 3.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 4.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 5.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme