thiane-3,5-dione

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

実験手順: A mixture of 2,2-dimethyl-5-(4-chloro-2-nitrobenzoyloxy)-3,6-dihydro-2H-thiopyran-3-one (8.3 g, 24.3 mmol), triethylamine (6.8 ml, 48.7 mmol) and acetone cyanohydrin (0.5 ml) in 35 ml of acetonitrile is stirred at RT for 16 hours. The reaction mixture is concentrated and taken up in ether. The ether extracts are washed with dilute HCl and with brine, dried and evaporated to dryness. The crude product is purified to give 2-2-dimethyl.4.(4.chloro.2.nitrobenzoyl).2H-thiopyran-3,5-(4H,6H)-dione (compound 1, Table A). The reaction mixture is concentrated The ether extracts are washed with dilute HCl and with brine dried evaporated to dryness The crude product is purified to give 2-2-dimethyl

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

実験手順: A mixture of 2,2-dimethyl-5-(4-chloro-2-nitrobenzoyloxy)-3,6-dihydro-2H-thiopyran-3-one (8.3 g, 24.3 mmol), triethylamine (6.8 ml, 48.7 mmol) and acetone cyanohydrin (0.5 ml) in 35 ml of acetonitrile is stirred at RT for 16 hours. The reaction mixture is concentrated and taken up in ether. The ether extracts are washed with dilute HCl and with brine, dried and evaporated to dryness. The crude product is purified to give 2-2-dimethyl.4.(4.chloro.2.nitrobenzoyl).2H-thiopyran-3,5-(4H,6H)-dione (compound 1, Table A). The reaction mixture is concentrated The ether extracts are washed with dilute HCl and with brine dried evaporated to dryness The crude product is purified to give 2-2-dimethyl

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

実験手順: A solution of 3,5-thiopyrandione (0.13 g, 1 mmol), 3-bromo-4-fluorobenzaldehyde(0.203 g, 1 mmol), and 3-aminopyrazole (0.082 g, 1 mmol) in ethanol (2 mL) was heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.045 g (12%) of the title compound. at reflux for 24 hours the volatiles were evaporated at reduced pressure the resulting residue was chromatographed on silica gel eluting with 5% ethanol/methylene chloride

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

実験手順: A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and fried for 16 hours under high vacuum to provide the title compound (0.13 g). cooled to ambient temperature The resulting solid was collected by filtration washed with ethanol and fried for 16 hours under high vacuum

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

実験手順: A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and dried for 16 hours under high vacuum to provide the title compound (0.13 g). cooled to ambient temperature The resulting solid was collected by filtration washed with ethanol dried for 16 hours under high vacuum

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

実験手順: A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and dried for 16 hours under high vacuum to provide the title compound (0.13 g). cooled to ambient temperature The resulting solid was collected by filtration washed with ethanol dried for 16 hours under high vacuum

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

実験手順: A solution of 3,5-thiopyrandione (0.13 g, 1 mmol) prepared as described in (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244), 3-bromo-4-fluorobenzaldehyde (0.203 g, 1 mmol), and 3-aminopyrazole (0.082 g, 1 mmol) in ethanol (2 mL) were heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.045 g (12%) of the title compound. at reflux for 24 hours the volatiles were evaporated at reduced pressure the resulting residue was chromatographed on silica gel eluting with 5% ethanol/methylene chloride

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

実験手順: A mixture of 2,2-dimethyl-5-(4-chloro-2-nitrobenzoyloxy)-3,6-dihydro-2H-thiopyran-3-one (8.3 g, 24.3 mmol), triethylamine (6.8 ml, 48.7 mmol) and acetone cyanohydrin (0.5 ml) in 35 ml of acetonitrile is stirred at RT for 16 hours. The reaction mixture is concentrated and taken up in ether. The ether extracts are washed with dilute HCl and with brine, dried and evaporated to dryness. The crude product is purified to give 2-2-dimethyl.4.(4.chloro.2.nitrobenzoyl).2H-thiopyran-3,5-(4H,6H)-dione (compound 1, Table A). The reaction mixture is concentrated The ether extracts are washed with dilute HCl and with brine dried evaporated to dryness The crude product is purified to give 2-2-dimethyl

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

実験手順: A solution of 3,5-thiopyrandione (0.13 g, 1 mmol), 3-bromo-4-fluorobenzaldehyde(0.203 g, 1 mmol), and 3-aminopyrazole (0.082 g, 1 mmol) in ethanol (2 mL) was heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.045 g (12%) of the title compound. at reflux for 24 hours the volatiles were evaporated at reduced pressure the resulting residue was chromatographed on silica gel eluting with 5% ethanol/methylene chloride

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

実験手順: A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and fried for 16 hours under high vacuum to provide the title compound (0.13 g). cooled to ambient temperature The resulting solid was collected by filtration washed with ethanol and fried for 16 hours under high vacuum

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

実験手順: A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and dried for 16 hours under high vacuum to provide the title compound (0.13 g). cooled to ambient temperature The resulting solid was collected by filtration washed with ethanol dried for 16 hours under high vacuum