3,5-bis(ethoxycarbonyl)-2,6-diethylpyridine 1-oxide; Me4tBuXPhosAuNTf2 in 1,2-dichloro-ethane T=20°C;

sodium in toluene 4 h; Heating;

in acetone 6 h; Ambient temperatureIrradiation;

1: 100 percent / 1,4-diazabicyclo<2.2.2>octane / 20 h / Heating 2: 74 percent / aq. sodium hydroxide / 6 h / Heating 3: 1.) triethylamine, diphenyl phosphorazidate, 2.) conc. HCl / 1.) toluene, 80-85 deg C, 1.5 h, 2.) reflux, 2 h View Scheme

hydrogenchloride; diphenyl phosphoryl azide; triethylamine 1.) toluene, 80-85 deg C, 1.5 h, 2.) reflux, 2 h; Multistep reaction;

1: 74 percent / aq. sodium hydroxide / 6 h / Heating 2: 1.) triethylamine, diphenyl phosphorazidate, 2.) conc. HCl / 1.) toluene, 80-85 deg C, 1.5 h, 2.) reflux, 2 h View Scheme

1: 1.) potassium metabisulfite / 1.) 50 deg C, water 2.) water, ether, 5 deg C, 6 h 2: stannous chloride dihydrate, cc. hydrogen chloride, acetic acid, hydrogen iodide / 3 h / Heating 3: 65 percent / cc. sulfuric acid / 12 h / Heating 4: sodium / toluene / 4 h / Heating View Scheme

1: stannous chloride dihydrate, cc. hydrogen chloride, acetic acid, hydrogen iodide / 3 h / Heating 2: 65 percent / cc. sulfuric acid / 12 h / Heating 3: sodium / toluene / 4 h / Heating View Scheme

1: 60 percent / Reimer-Tiemann reaction 2: 80 percent / potassium carbonate, potassium iodide / 4 h / Heating 3: 1.) potassium metabisulfite / 1.) 50 deg C, water 2.) water, ether, 5 deg C, 6 h 4: stannous chloride dihydrate, cc. hydrogen chloride, acetic acid, hydrogen iodide / 3 h / Heating 5: 65 percent / cc. sulfuric acid / 12 h / Heating 6: sodium / toluene / 4 h / Heating View Scheme

1: 65 percent / cc. sulfuric acid / 12 h / Heating 2: sodium / toluene / 4 h / Heating View Scheme