2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 48 h; Heating;

1: 98 percent / copper(II) nitrate trihydrate / acetic anhydride / 24 h / Ambient temperature 2: 95 percent / DDQ / nitrobenzene / 0.67 h / Heating View Scheme

1: 68 percent / triphenyltin hydride, triethylamine / acetonitrile / 1 h / Irradiation 2: 98 percent / copper(II) nitrate trihydrate / acetic anhydride / 24 h / Ambient temperature 3: 95 percent / DDQ / nitrobenzene / 0.67 h / Heating View Scheme

(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

hydrazine hydrate; palladium on activated charcoal in ethanol; benzene

hydrazine hydrate; palladium on activated charcoal in tetrahydrofuran T=0°C; 1 h;