1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C View Scheme

N,N,N',N'-tetramethylguanidine; 4-nitrobenzaldoxime in 1,4-dioxane; water T=20°C; 0.05 h;

ammonia in methanol T=20°C; 5 h;

1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min View Scheme

Multi-step reaction with 3 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C2: pyridine / 1 h / 20 °C3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h  

Multi-step reaction with 3 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C2: pyridine / 1 h / 20 °C3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h  

Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C2: pyridine / 1 h / 20 °C3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h4: acetonitrile / 8 h / 20 °C5: 1.) triethylamine, 2.) acetic anhydride, pyridine / 1.) ethanol, 20 deg C, 10 min