benzene-1,2,4,5-tetrol

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (10.00 g, 71.43 mmol) was suspended in water (200 ml, distilled) followed by HCl (6 mL, 142-86 mmol, conc.). Iron (4.00 g, 71.43 mmol, powder) was added and the mixture was stirred 30 minutes at room temperature. The solution was filtered and the solution evaporated to dryness. The product was isolated as a grey brown powder containing some iron complexes. Yield 14.80 g. The product is used as such in the reaction with acetone and P2O5 (Example 5) with no negative effects. The solution was filtered the solution evaporated to dryness The product was isolated as a grey brown powder

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (4.00 g, 28.55 mmol) was suspended in water (50 ml, distilled) followed by Na2S2O4 (10.00 g, 57.47 mmol) and HCl (5.5 g, 55.75 mmol conc. soln.). The mixture was stirred 30 min. at room temperature and evaporated to dryness. The residue was washed with THF (40 ml) and filtered. The THF was evaporated yielding 2.00 g (14.07 mmol, 49.3%) of the title substance. evaporated to dryness The residue was washed with THF (40 ml) filtered The THF was evaporated yielding 2.00 g (14.07 mmol, 49.3%) of the title substance

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

Procedure: 18.6 g of the 1,2,4,5-tetrahydroxybenzene prepared according to Example 4 (0.13 mole) and 70 ml acetone (58.6 g, 1.0 mole) was dissolved in 1 1 tetrahydrofuran. 168 g P2O5 (1.18 mole) was added to the vigorously stirred mixture in portions as fast as possible. The mixture was heated to reflux for 4 hours. After cooling to room temperature the solids were filtered with suction and washed with 0.5 L ether. The combined filtrates were treated with 10 g K2CO3 and stirred 1 hour, filtered and evaporated to dryness yielding a yellow-brown oily solid. The product was triturated with petroleum ether, decanted and evaporated to yield 13.8 g of the title compound (48%) as white-yellow crystals, mp=122° C., which can be recrystalized from a small amount of petroleum ether. The mixture was heated to reflux for 4 hours were filtered with suction washed with 0.5 L ether The combined filtrates were treated with 10 g K2CO3 filtered evaporated to dryness yielding a yellow-brown oily solid The product was triturated with petroleum ether decanted evaporated

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (10.00 g, 71.43 mmol) was suspended in water (200 ml, distilled) followed by HCl (6 mL, 142-86 mmol, conc.). Iron (4.00 g, 71.43 mmol, powder) was added and the mixture was stirred 30 minutes at room temperature. The solution was filtered and the solution evaporated to dryness. The product was isolated as a grey brown powder containing some iron complexes. Yield 14.80 g. The product is used as such in the reaction with acetone and P2O5 (Example 5) with no negative effects. The solution was filtered the solution evaporated to dryness The product was isolated as a grey brown powder

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (10.00 g, 71.43 mmol) was suspended in water (200 ml, distilled) followed by HCl (6 mL, 142-86 mmol, conc.). Iron (4.00 g, 71.43 mmol, powder) was added and the mixture was stirred 30 minutes at room temperature. The solution was filtered and the solution evaporated to dryness. The product was isolated as a grey brown powder containing some iron complexes. Yield 14.80 g. The product is used as such in the reaction with acetone and P2O5 (Example 5) with no negative effects. The solution was filtered the solution evaporated to dryness The product was isolated as a grey brown powder

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (4.00 g, 28.55 mmol) was suspended in water (50 ml, distilled) followed by Na2S2O4 (10.00 g, 57.47 mmol) and HCl (5.5 g, 55.75 mmol conc. soln.). The mixture was stirred 30 min. at room temperature and evaporated to dryness. The residue was washed with THF (40 ml) and filtered. The THF was evaporated yielding 2.00 g (14.07 mmol, 49.3%) of the title substance. evaporated to dryness The residue was washed with THF (40 ml) filtered The THF was evaporated yielding 2.00 g (14.07 mmol, 49.3%) of the title substance

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

Procedure: 18.6 g of the 1,2,4,5-tetrahydroxybenzene prepared according to Example 4 (0.13 mole) and 70 ml acetone (58.6 g, 1.0 mole) was dissolved in 1 1 tetrahydrofuran. 168 g P2O5 (1.18 mole) was added to the vigorously stirred mixture in portions as fast as possible. The mixture was heated to reflux for 4 hours. After cooling to room temperature the solids were filtered with suction and washed with 0.5 L ether. The combined filtrates were treated with 10 g K2CO3 and stirred 1 hour, filtered and evaporated to dryness yielding a yellow-brown oily solid. The product was triturated with petroleum ether, decanted and evaporated to yield 13.8 g of the title compound (48%) as white-yellow crystals, mp=122° C., which can be recrystalized from a small amount of petroleum ether. The mixture was heated to reflux for 4 hours were filtered with suction washed with 0.5 L ether The combined filtrates were treated with 10 g K2CO3 filtered evaporated to dryness yielding a yellow-brown oily solid The product was triturated with petroleum ether decanted evaporated

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

Procedure: In some particular embodiments, one molar unit of the 1,2,4,5-tetrahydroxybenzene compound is reacted with about one molar unit of a first 1,2-diaminobenzene compound to form an intermediate, and the intermediate is subsequently reacted with about one molar unit of a second 1,2-diaminobenzene compound to form the 5,7,12,14-tetrahydro-5,7,12,14-tetraazapentacene compound. The first 1,2-diaminobenzene compound and the second 1,2-diaminobenzene compound are different. to form an intermediate

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

Procedure: Alternatively, the at least one 1,2-diaminobenzene compound and the 1,2,4,5-tetrahydroxybenzene compound are dissolved in a solvent to form a solution, and the solution is heated to form the 5,7,12,14-tetrahydro-5,7,12,14-tetraazapentacene compound. The solution can be heated at a temperature of from about 80° C. to about 180° C., and the solution can be heated for a time period of from about 30 minutes to about 12 hours. to form a solution the solution is heated

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

Procedure: Alternatively, the at least one 1,2-diaminobenzene compound and the 1,2,4,5-tetrahydroxybenzene compound can be combined to form a mixture, and the mixture is then heated in an inert environment to form the 5,7,12,14-tetrahydro-5,7,12,14-tetraazapentacene compound. The mixture can be heated at a temperature above 300° C., and the mixture can be heated for a time period of from about 30 seconds to about 10 minutes. to form a mixture the mixture is then heated in an inert environment

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

Procedure: The at least one 1,2-diaminobenzene compound and the 1,2,4,5-tetrahydroxybenzene compound can be combined to form a mixture, and the mixture is then heated in an inert environment to form the 5,7,12,14-tetrahydro-5,7,12,14-tetraazapentacene compound. The mixture can be heated at a temperature of from about 110° C. to about 250° C., and the mixture can be heated for a time period of from about 30 minutes to about 12 hours. to form a mixture the mixture is then heated in an inert environment

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

Procedure: 2,5-Dihydroxy-1,4-benzoquinone (10.00 g, 71.43 mmol) was suspended in water (200 ml, distilled) followed by HCl (6 mL, 142.86 mmol, conc.). Iron (4.00 g, 71.43 mmol, powder) was added and the mixture was stirred 30 minutes at room temperature. The solution was filtered and the solution evaporated to dryness. The product was isolated as a grey brown powder containing some iron complexes. Yield 14.80 g. The product is used as such in the reaction with acetone and P2O5 (Example 5) with no negative effects. The solution was filtered the solution evaporated to dryness The product was isolated as a grey brown powder