1: 87 percent / piperidine, 95percent ethanol / 18 h / Heating 2: 45 percent / KOH / aq. ethanol / 6 h / Heating 3: SeO2 / acetic acid / 2 h / 80 °C View Scheme

1: para-bromobenzonitrile; acetylacetone With dichloro(cycloocta-1,5-diene)palladium(II); triethylamine; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in 1,4-dioxane T=80°C; GloveboxInert atmosphere; 2: COgen With dichloro(cycloocta-1,5-diene)palladium(II); N,N-dicyclohexylmethylamine; [(t-Bu)3PH]BF4 in 1,4-dioxane T=80°C; GloveboxInert atmosphere; Further stages;

hydrogenchloride in water T=80°C; 1 h;

in tetrahydrofuran; hexane T=-78°C; 0.0833333 h;

1: L-proline / dimethyl sulfoxide / 5 h / 20 °C / |Inert atmosphere 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2 h / 0 °C / |Inert atmosphere; |Reflux View Scheme

sodium hydride 1) THF, 2) reflux, 1.5 h; Yield given. Multistep reaction;

sodium amide in diethyl ether