Multi-step reaction with 16 steps
1: 1.) H2; 2.) N2H4, base
2: 71 percent / Br2 / CCl4 / 1 h / 140 °C / Irradiation
3: 33 percent / DMSO
4: 1.) NaH / 1.) THF; 2.) 14 h, room temp.
5: 60 percent / CH3C6H4SO2N3, NEt3 / tetrahydrofuran / 24 h / Ambient temperature
6: 51 percent / methanol / 5 h / -50 °C / Irradiation
7: 90 percent / KOH / ethanol / 12 h / 80 °C
8: DMAP, DCC / CH2Cl2
9: 82 percent / t-BuSH / benzene / 7 h / Heating
10: 78 percent / Br2 / CCl4 / 1 h / 140 °C / Irradiation
11: 77 percent / DBU / dimethylformamide / 16 h / 150 °C
12: 1.) B2H6; 2.) NaOH, 30 percent H2O2 / 1.) THF, 0 deg C, 1 h; room temp., 12 h; 2.) 40 deg C, 4 h
13: 1.) ClCOCOCl, DMSO; 2.) NEt3 / 1.) -50 deg C; 2.) -50 deg C to room temp.
14: 1.) NaH / 1.) THF; 2.) 14 h, room temp.
15: 14 percent / CH3C6H4SO2N3, NEt3 / tetrahydrofuran / 24 h / Ambient temperature
16: 45 percent / dioxane; H2O / 0 °C / Irradiation
With
dmap; potassium hydroxide; sodium hydroxide; oxalyl dichloride; hydrogen; dihydrogen peroxide; bromine; sodium hydride; 2-methylpropan-2-thiol; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; diborane; hydrazine;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;