hydrazine in methanol 1 h; Heating / reflux;

1: With N-(diphenylmethylene)amine; palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in toluene T=20°C; 0.333333 h; Inert atmosphere; 2: With sodium t-butanolate in toluene T=80 - 85°C; 2 h; Inert atmosphere;

in ethanol Reflux; regioselective reaction;

1.1: dimethyl sulfoxide / 24 h / 20 - 85 °C 2.1: N-(diphenylmethylene)amine / palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / toluene / 0.33 h / 20 °C / Inert atmosphere 2.2: 2 h / 80 - 85 °C / Inert atmosphere View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.92 h / -70 °C 1.2: 20 °C 2.1: dimethyl sulfoxide / 24 h / 20 - 85 °C 3.1: N-(diphenylmethylene)amine / palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / toluene / 0.33 h / 20 °C / Inert atmosphere 3.2: 2 h / 80 - 85 °C / Inert atmosphere View Scheme

1: 87 percent / dioxane / 5 h / 120 °C 2: sodium carbonate / dimethylformamide / 12 h / 80 °C 3: 85percent hydrazine hydrate / ethanol / 3 h View Scheme

1: sodium carbonate / dimethylformamide / 12 h / 80 °C 2: 85percent hydrazine hydrate / ethanol / 3 h View Scheme

tert.-butylnitrite in tetrahydrofuran 1 h; Reflux;