2-diazocyclohexane-1,3-dione

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in the Example 1, using 2-diazo-cyclohexane-1,3-dione and 3-bromo-4-fluoroaniline as starting materials to yield the title compound as a white solid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in the Example 1, using 2-diazo-cyclohexane-1,3-dione and 3-iodoaniline as starting materials to yield the title compound as a white solid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in the Example 1, using 2-diazo-cyclohexane-1,3-dione and 3-iodoaniline as starting materials to yield the title compound as a white solid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in the Example 1, using 2-diazo-cyclohexane-1,3-dione and 3,4-difluoroaniline as starting materials to yield the title compound as a white solid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in the Example 1, using 2-diazo-cyclohexane-1,3-dione and 3,4-difluoroaniline as starting materials to yield the title compound as a white solid.

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Diazo-cyclohexane-1,3-dione (2 mmoL), prepared by the literature known procedure, 3-cyano-aniline (1 mmoL) and rhodium acetate dimmer (0.01 mmoL) in benzene (10 mL) were heated at 80° C. for 4˜6 hrs. The solid was filtered off and the filtrate was concentrated to give a yellow oil, which was purified by silica gel chromatography to afford the title compound as a white solid. The solid was filtered off the filtrate was concentrated to give a yellow oil, which was purified by silica gel chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-acetamidobenzenesulphonylazide (25 g, 104 mmol) and triethylamine (36 ml, 250 mmol) in dichloromethane maintained at a temperature below 30° C. by external cooling is treated dropwise by a solution of cyclohexane-1,3-dione (13 g, 115 mmol) in 200 ml of dichloromethane. The reaction mixture is stirred for 75 minutes at ambient temperature then filtered on Celite. After concentration to approximately 300 ml, the filtrate is washed with water then dried over sodium sulphate. The brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure is similar to that obtained in Example 55.1, and is used as it is in the following stage. maintained at a temperature below 30° C. by external cooling then filtered on Celite After concentration to approximately 300 ml the filtrate is washed with water then dried over sodium sulphate The brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure that obtained in Example 55.1

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of rhodium acetate (32 mg, 72 μmol) and 2-fluorobenzonitrile (2.31 ml; 22 mmol) in perfluorobenzene (5 ml) is treated at 60° C. dropwise by a solution of diazocyclohexanedione (obtained in Stage 66.1; 1 g; 7.24 mmol) in 5 ml of perfluorobenzene. The reaction medium is maintained at 60° C. until exhaustion of the release of nitrogen (1 hour; TLC on SiO2: 2% MeOH/CH2Cl2). After cooling down to ambient temperature and filtration, the solvent of the filtrate is evaporated. The residue is purified by chromatography (SiO2: AcOEt/heptane: 1/1) in order to produce a light yellow powder. After cooling down to ambient temperature filtration the solvent of the filtrate is evaporated The residue is purified by chromatography (SiO2: AcOEt/heptane: 1/1) in order to produce a light yellow powder

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-acetamidobenzenesulphonylazide (25 g, 104 mmol) and triethylamine (36 ml, 250 mmol) in dichloromethane maintained at a temperature below 30° C. by external cooling is treated dropwise by a solution of cyclohexane-1,3-dione (13 g, 115 mmol) in 200 ml of dichloromethane. The reaction mixture is stirred for 75 minutes at ambient temperature then filtered on Celite. After concentration to approximately 300 ml, the filtrate is washed with water then dried over sodium sulphate. The brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure is similar to that obtained in Example 55.1, and is used as it is in the following stage. maintained at a temperature below 30° C. by external cooling then filtered on Celite After concentration to approximately 300 ml the filtrate is washed with water then dried over sodium sulphate The brown-yellow solid (14 g; 88%) obtained by evaporation of the solvent under reduced pressure that obtained in Example 55.1