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With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxaneInert atmosphere; Reflux
A mixture of 6-chloro-3,4-dihydro-2H-isoquinolin-l-one (181.5 mg, 1 mmol, intermediate A-2) and DDQ (227 mg, 1 mmol) in dioxane (3 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was treated with satd. aq. NaHC03 solution, and then extracted with ethyl acetate (2 x 10 mL). The organic layers were dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford a crude product which was then purified by silica gel flash chromatography to give title compound (108 mg, 60percent) as a white solid. MS: 180.0 (M+H+).
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane;Inert atmosphere; Reflux;
A mixture of 6-chloro-3,4-dihydro-2H-isoquinolin-l-one (181.5 mg, 1 mmol, intermediate A-2) and DDQ (227 mg, 1 mmol) in dioxane (3 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was treated with satd. aq. NaHC03 solution, and then extracted with ethyl acetate (2 x 10 mL). The organic layers were dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford a crude product which was then purified by silica gel flash chromatography to give title compound (108 mg, 60%) as a white solid. MS: 180.0 (M+H+).
4-(4-methylphenylthio)-6-chloroisoquinolin-1(2H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90.0℃; for 10.0h;High pressure;
6-chloroisoquinolin-1 (2H)-one (10 mmol), bis(4-methylphenyl) disulfide (10 mmol), hexafluoride was sequentially added to a pressure-resistant reaction tube at room temperature. Silver acetate (10 mmol) and dichloroethene (9 mL). The reaction mixture was then reacted at 90 C for 10 hours. The reaction was quenched and concentrated under reduced pressure to give a crude material which was washed with a mixture of petroleum ether and ethyl acetate. Fast column chromatography to obtain the corresponding product 4-(4-Methylphenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 90%;
6-chloro-4-((2-fluorophenyl)thio)isoquinolin-1(2H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90℃; for 10h;High pressure;
6-chloroisoquinolin-1 (2Eta)-one (12 mmol), bis(2-fluorophenyl)disulfide (10 mmol), hexafluoroantimonic acid were sequentially added to a pressure-resistant reaction tube at room temperature. Silver (10 mmol) and dichloroethane (6 mL). The reaction mixture was then reacted at 90 C for 10 hours. The reaction was stopped, concentrated under reduced pressure to give a crude material, which was washed with a mixture of petroleum ether and ethyl acetate. 4-(2-Fluorophenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 70%;
6-chloro-4-((4-methoxyphenyl)thio)isoquinolin-1(2H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90.0℃; for 10.0h;High pressure;
6-chloroisoquinolin-1 (2Eta)-one (12mm0l), bis(4-methoxyphenyl)disulfide (10mmol), hexafluorofluoride was sequentially added to the pressure resistant reaction tube at room temperature. Place silver acid (10 mmol) and dichloroethene (6 mL). Then the reaction mixture is at 90 C Reaction for 10 hours. The reaction was quenched and concentrated under reduced pressure to give a crude material which was washed with a mixture of petroleum ether and ethyl acetate. Flash column chromatography gave the corresponding product 4-(4-methoxyphenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 87%;
6-chloro-4-(phenylthio)isoquinolin-1(2H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 100.0℃; for 8.0h;High pressure;
6-chloroisoquinolin-1 (2Eta)-one (12 mmol), diphenyl disulfide (10 mmol), silver hexafluoroantimonate (12 mmol) and 6 parts were sequentially added to a pressure-resistant reaction tube at room temperature. Dichloroethane (6 mL). The reaction mixture was then reacted at 100 C for 8 hours. The reaction was stopped, concentrated under reduced pressure to give a crude material, which was washed with a mixture of petroleum ether and ethyl acetate. 4-phenylthio-6-chloroisoquinolin-1 (2H)-one. Yield 80%;
6-chloro-4-((3-fluorophenyl)thio)isoquinolin-1(2H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90.0℃; for 10.0h;High pressure;
6-chloroisoquinolin-1 (2H)-one (12 mmol), bis(3-fluorophenyl)disulfide (10 mmol), hexafluoroantimonic acid were sequentially added to a pressure-resistant reaction tube at room temperature. Silver (10 mmol) and dichloroethane (6 mL). The reaction mixture was then reacted at 90 C for 10 hours. The reaction was stopped, concentrated under reduced pressure to give a crude material, which was washed with a mixture of petroleum ether and ethyl acetate. 4-(3-Fluorophenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 88%;
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; potassium hydrogencarbonate; In benzonitrile; at 80.0℃; for 24.0h;
General procedure: The preparation steps are as follows: In the air, add a magnetic tube, benzoic acid (0.25mmol, 30.5mg), N-vinylformamide (1.5mmol, 106uL), [Cp * RhCl2] 2 (5mol %, 10.2 mg), AgOAc (0.25 mmol, 42 mg), KHCO3 (0.05 mmol, 5 mg) and benzonitrile (1.25 mL).Then plug in the rubber plug.Heat and stir in an 80 C oil bath for 24h.After the reaction is completed, the reaction system is cooled to room temperature,Filter with a glass sand funnel with diatomaceous earth,And washed with dichloromethane and ethyl acetate,The filtrates were combined, the solvent was distilled off under reduced pressure, petroleum ether / ethyl acetate (3: 1) was used as the mobile phase, and the product was purified by flash silica gel column chromatography.The yield of this example is 79%.
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