1,3-diiodopropane

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane (1.1.20) was prepared by reacting (1.1.3) with two equivalents of p-toluenesulfonyl chloride. Two equivalents of N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane (1.1.20) hydrobromide were reacted with one equivalent of 1,3-diiodopropane in acetonitrile with excess potassium carbonate. 1,3-Bis[N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane propane (1.1.21) was isolated and purified by chromatography. The p-toluenesulfonyl groups were removed using sulfuric acid and HBr to yield the title compound (1.1.19). ##STR8## 1.1.22 1,4,7,10-Tetraazabicyclo[5.5.2]tetradecane

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

実験手順: To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 296 mg. (1 mmole) of 1,3-diiodopropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether. the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration The filtrate is evaporated the solid residue obtained is extracted with methylene chloride The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether

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

実験手順: To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 296 mg. (1 mmole) of 1,3-diiodopropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether. the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration The filtrate is evaporated the solid residue obtained is extracted with methylene chloride The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether

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

実験手順: To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 296 mg. (1 mmole) 1,3-diiodopropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether. the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration The filtrate is evaporated the solid residue obtained is extracted with methylene chloride The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether

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

実験手順: To a flask were added 2 g 2-mercapto-5-methylbenzimidazole, 4.2 g potassium carbonate, 4.0 g 1,3-diiodopropane and 60 ml N,N-dimethylformamide. The mixture was heated to 50 C under nitrogen for 5 hours and then cooled to 22 C. The reaction was quenched with 100 ml water and the product was extracted twice with ethyl acetate and washed twice with water. Following removal of the solvent, the product was recrystallized by dissolving in a hot mixture of 50 ml hexane with 10 ml 2-propanol. After cooling to 5 C, the product was filtered, washed with hexane and dried giving 0.63 g of an off-white solid. The mixture was heated to 50 C under nitrogen for 5 hours cooled to 22 C The reaction was quenched with 100 ml water the product was extracted twice with ethyl acetate washed twice with water removal of the solvent the product was recrystallized by dissolving in a hot mixture of 50 ml hexane with 10 ml 2-propanol After cooling to 5 C the product was filtered washed with hexane dried

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

実験手順: N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane (1.1.20) was prepared by reacting (1.1.3) with two equivalents of p-toluenesulfonyl chloride. Two equivalents of N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane (1.1.20) hydrobromide were reacted with one equivalent of 1,3-diiodopropane in acetonitrile with excess potassium carbonate. 1,3-Bis[N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane propane (1.1.21) was isolated and purified by chromatography. The p-toluenesulfonyl groups were removed using sulfuric acid and HBr to yield the title compound (1.1.19). ##STR8## 1.1.22 1,4,7,10-Tetraazabicyclo[5.5.2]tetradecane

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

実験手順: To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 296 mg. (1 mmole) of 1,3-diiodopropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether. the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration The filtrate is evaporated the solid residue obtained is extracted with methylene chloride The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether

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

実験手順: To a solution of methyl methylsulfonylacetate (1.0 g, 6.6 mmol) in 20 mL of acetonitrile was added 1,3-diiodopropane (2.3 mL, 20 mmol) and cesium carbonate (6.4 g, 20 mmol). After stirring at room temperature for 2 h, the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane to give methyl 1-methylsulfonylcyclobutanecarboxlate (1.0 g, 79%). δ 3.84 (s, 3H), 3.02 (s, 3H), 2.84-2.65 (m, 4H), 2.25-2.02 (m, 2H). the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL) The organic layer was separated dried over anhydrous magnesium sulfate filtered concentrated to dryness the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A pressure tube, equipped with a magnetic stirring bar, was charged with Compound 2 (0.54 g, 3 mmole) and 1,3-diiodopropane (2.66 g, 9 mmole). The mixture was heated to ˜120° C. for 3 hours. The residue was extensively washed with ethyl acetate and diethyl ether and dried under vacuum to give 0.4 g of yellow solid Compound 3 (yield ˜28%). A pressure tube, equipped with a magnetic stirring bar The residue was extensively washed with ethyl acetate and diethyl ether dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of methyl methylsulfonylacetate (1.0 g, 6.6 mmol) in 20 mL of acetonitrile was added 1,3-diiodopropane (2.3 mL, 20 mmol) and cesium carbonate (6.4 g, 20 mmol). After stirring at room temperature for 2 h, the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane to give methyl 1-methylsulfonylcyclobutanecarboxlate (1.0 g, 79%). δ 3.84 (s, 3H), 3.02 (s, 3H), 2.84-2.65 (m, 4H), 2.25-2.02 (m, 2H). the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL) The organic layer was separated dried over anhydrous magnesium sulfate filtered concentrated to dryness the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane