copper(l) iodide in acetonitrile T=20°C; 2 h; Photolysis;

tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 6 h;

in o-xylene T=150°C; Cyclization;

1: in N,N-dimethyl-formamide T=120°C; 8 h; 2: With water in N,N-dimethyl-formamide T=20°C;

1.1: 85 percent / K2CO3; dibenzo-18-crown-6 / CH2Cl2 / 16 h / 20 °C 2.1: tetrahydrofuran / 1 h / 20 °C 3.1: 14 percent / HCl; H2O / tetrahydrofuran / 24 h / 20 °C 4.1: Et3N / CH2Cl2 / 1 h / 20 °C 5.1: 80 percent / nitrobenzene / 0.2 h / 150 °C / microwave irradiation 6.1: 82 percent / K2CO3 / dimethylformamide / 2 h / 60 °C 7.1: 91 percent / H2 / Pd/C / ethanol / 5 h / 20 °C 8.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 8.2: 85 percent / NaN3 / H2O / 5 h / 20 °C 9.1: 82 percent / o-xylene / 20 h / 150 °C View Scheme

1.1: 85 percent / K2CO3; dibenzo-18-crown-6 / CH2Cl2 / 16 h / 20 °C 2.1: tetrahydrofuran / 1 h / 20 °C 3.1: 14 percent / HCl; H2O / tetrahydrofuran / 24 h / 20 °C 4.1: Et3N / CH2Cl2 / 1 h / 20 °C 5.1: 80 percent / nitrobenzene / 0.2 h / 150 °C / microwave irradiation 6.1: 82 percent / K2CO3 / dimethylformamide / 2 h / 60 °C 7.1: 91 percent / H2 / Pd/C / ethanol / 5 h / 20 °C 8.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 8.2: 85 percent / NaN3 / H2O / 5 h / 20 °C 9.1: 82 percent / o-xylene / 20 h / 150 °C View Scheme

oxygen; palladium on activated charcoal in diphenylether 48 h; Heating;

acetic acid 2 h; Heating;

iron; acetic acid 1 h; Reflux;

palladium on activated charcoal in xylene 12 h; Heating;