1a-methyl-7aH-naphtho[2,3-b]oxirene-2,7-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Menadione crystalline (1) (5 g, 29.04 mmol, 1 equivalent) and 2 M NaOH (7.26 mL, 14.52 mmol, 0.5 equivalents) are dissolved in a mixture of methanol/water 4:1 (50 mL) at 0-2° C. After stirring at this temperature for 10 minutes, 35% hydrogen peroxide is added (4.2 mL, 43.56 mmol, 1.5 equivalents). Work-up: after 30 minutes at 0° C. the product is extracted with ethyl ether. The organic phase is dried over Na2SO4 and evaporated under reduced pressure. A whitish powder is obtained (5 g, 26.57 mmol). Yield: 91.5%. after 30 minutes at 0° C. the product is extracted with ethyl ether The organic phase is dried over Na2SO4 evaporated under reduced pressure A whitish powder is obtained (5 g, 26.57 mmol)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50°C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evpaorated, giving 1 g of the desired product as a viscous red oil. The solvent was then removed the remainder filtered through a one inch plug of silica gel eluted with chloroform

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50°C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evpaorated, giving 1 g of the desired product as a viscous red oil. The solvent was then removed the remainder filtered through a one inch plug of silica gel eluted with chloroform

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Flowchart V, 2,3-epoxy-2-methyl-1,4-naphthoquinone 11 is reacted with an amine 2, where R2, R3, R4 and R5 are as described above, in absolute ethanol with heat for several hours, producing the 3-methyl-1,4-naphthalenedione derivatives 12. with heat for several hours

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50° C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evaporated, giving 1 g of the desired product as a viscous red oil. The solvent was then removed the remainder filtered through a one inch plug of silica gel eluted with chloroform The eluate was evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Flowchart V, 2,3-epoxy-2-methyl-1,4-naphthoquinone 11 is reacted with an amine 2, where R2, R3, R4 and R5 are as described above, in absolute ethanol with heat for several hours, producing the 3-methyl-1,4-naphthalenedione derivatives 12. with heat for several hours

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.88 g of 2,3-epoxy-3-methyl-1, 4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50° C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evpaorated, giving 1 g of the desired product as a viscous red oil. The solvent was then removed the remainder filtered through a one inch plug of silica gel eluted with chloroform

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Flowchart V, 2,3-epoxy-2-methyl-1,4-naphthoquinone 11 is reacted with an amine 2, where R2, R3, R4 and R5 are as described above, in absolute ethanol with heat for several hours, producing the 3-methyl-1,4-naphthalenedione derivatives 12. with heat for several hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Menadione crystalline (1) (5 g, 29.04 mmol, 1 equivalent) and 2 M NaOH (7.26 mL, 14.52 mmol, 0.5 equivalents) are dissolved in a mixture of methanol/water 4:1 (50 mL) at 0-2° C. After stirring at this temperature for 10 minutes, 35% hydrogen peroxide is added (4.2 mL, 43.56 mmol, 1.5 equivalents). Work-up: after 30 minutes at 0° C. the product is extracted with ethyl ether. The organic phase is dried over Na2SO4 and evaporated under reduced pressure. A whitish powder is obtained (5 g, 26.57 mmol). Yield: 91.5%. after 30 minutes at 0° C. the product is extracted with ethyl ether The organic phase is dried over Na2SO4 evaporated under reduced pressure A whitish powder is obtained (5 g, 26.57 mmol)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50°C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evpaorated, giving 1 g of the desired product as a viscous red oil. The solvent was then removed the remainder filtered through a one inch plug of silica gel eluted with chloroform

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Flowchart V, 2,3-epoxy-2-methyl-1,4-naphthoquinone 11 is reacted with an amine 2, where R2, R3, R4 and R5 are as described above, in absolute ethanol with heat for several hours, producing the 3-methyl-1,4-naphthalenedione derivatives 12. with heat for several hours