T=40°C; 2 h; Ionic liquidInert atmosphere;

0.25 h; Heating;

in acetonitrile T=20°C; 0.25 h;

in ethanol T=20°C;

in tetrahydrofuran T=300°C; Gould-Jacobs type cyclization; P=75007.5 Torr; 0.025 h; Flash vacuum pyrolysisAutoclave; regioselective reaction;

1.1: diphenylether / 0.5 h / 250 °C / |Inert atmosphere 2.1: acetic acid / 0.17 h / |Reflux 2.2: 2 h / |Reflux 3.1: trichlorophosphate / acetonitrile / 7 h / 20 °C / |Reflux View Scheme

in diphenylether T=250°C; 0.5 h; Inert atmosphere;

1: diphenylether / 0.5 h / 250 °C / |Inert atmosphere 2: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 20 °C 3: phosphorus oxytribromide / N,N-dimethyl-formamide / 3 h / 0 - 70 °C 4: palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / toluene / 1.5 h / 120 °C / |Inert atmosphere; |Microwave irradiation 5: bis-triphenylphosphine-palladium(II) chloride; sodium acetate / N,N-dimethyl acetamide / 1 h / 150 °C / |Inert atmosphere; |Microwave irradiation View Scheme

1.1: diphenylether / 0.5 h / 250 °C / |Inert atmosphere 2.1: acetic acid / 0.17 h / |Reflux 2.2: 2 h / |Reflux 3.1: trichlorophosphate / acetonitrile / 7 h / 20 °C / |Reflux 4.1: hydrogenchloride / dichloromethane; diethyl ether / 1 h / 5 - 20 °C 4.2: 5 h / |Reflux 5.1: palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / toluene / 1.5 h / 120 °C / |Inert atmosphere; |Microwave irradiation 6.1: bis-triphenylphosphine-palladium(II) chloride; sodium acetate / N,N-dimethyl acetamide / 1 h / 150 °C / |Inert atmosphere; |Microwave irradiation View Scheme

1: 1) LiH / 1) acetonitrile, 40 degC, 2 h, 2) room temp., 24 h 2: 82 percent / HOAc / 60 °C 3: 83.4 percent / H2 / Pd/C (10percent) / ethanol; acetic acid / 1 h View Scheme