1,8-diiodooctane

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in an 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.05 (1H, d, C1-H), 8.77 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.35 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.68 (2H, t, C′1-CH2), 2.00 (2H, m, C′2-CH2), 1.30 (4H, m, C′3&4-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in an 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in an 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.05 (1H, d, C1-H), 8.77 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.35 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.68 (2H, t, C′1-CH2), 2.00 (2H, m, C′2-CH2), 1.30 (4H, m, C′3&4-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in an 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in an 89% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.07 (1H, d, C6-H), 5.09 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.25 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.5, 25.7. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in an 89% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 93% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.11 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.59 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.28 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.6, 28.1, 25.2. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 93% yield

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

Procedure: To a cooled (-78° C.) solution of lithium diisopropylamide (20 mmol) in a mixture of THF (20 mL) and hexane (8 mL) (obtained in situ from the corresponding diisopropylamine and n-BuLi) was added slowly the compound obtained in step 1(3.96 g, 18 mmol) in anhyd. THF(10 mL). The mixture was stirred for 30 minutes and 1,8-diiodooctane (7.19 g, 20 mmol) in hexamethylphosphoramide (3.50 g, 20 mmol), was added. The mixture was stirred at -78° C. for 30 minutes, slowly brought to 0° C. over a period of 2 h and quenched by the cautious addition of 50 mL of 12% aqueous sodium chloride solution. The mixture was extracted with ether, washed with brine, dried and the solvent was evaporated. The crude product was purified to an oil (3.23 g) by a flash chromatography over silica using hexane to 1% EtOAc in hexane as an eluant; 1H NMR (300 MHz, CDCl3) δ: 7.35(m, 5H), 5.15(s,2H), 3.20(t,8 Hz,2H), 2.20(m, 1H), 2.0(m, 1H), 1.2-1.8(m,22H) The mixture was stirred at -78° C. for 30 minutes slowly brought to 0° C. over a period of 2 h quenched by the cautious addition of 50 mL of 12% aqueous sodium chloride solution The mixture was extracted with ether washed with brine dried the solvent was evaporated The crude product was purified to an oil (3.23 g) by a flash chromatography over silica

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

Procedure: To a cooled (-78° C.) solution of lithium diisopropylamide (20 mmol) in a mixture of THF (20 mL) and hexane (8 mL) (obtained in situ from the corresponding diisopropylamine and n-BuLi) was added slowly the compound obtained in step 1(3.96 g, 18 mmol) in anhyd. THF(10 mL). The mixture was stirred for 30 minutes and 1,8-diiodooctane (7.19 g, 20 mmol) in hexamethylphosphoramide (3.50 g, 20 mmol), was added. The mixture was stirred at -78° C. for 30 minutes, slowly brought to 0° C. over a period of 2 h and quenched by the cautious addition of 50 mL of 12% aqueous sodium chloride solution. The mixture was extracted with ether, washed with brine, dried and the solvent was evaporated. The crude product was purified to an oil (3.23 g) by a flash chromatography over silica using hexane to 1% EtOAc in hexane as an eluant; 1H NMR (300 MHz, CDCl3) δ: 7.35(m, 5H), 5.15(s,2H), 3.20(t,8 Hz,2H), 2.20(m, 1H), 2.0(m, 1H), 1.2-1.8(m,22H) The mixture was stirred at -78° C. for 30 minutes slowly brought to 0° C. over a period of 2 h quenched by the cautious addition of 50 mL of 12% aqueous sodium chloride solution The mixture was extracted with ether washed with brine dried the solvent was evaporated The crude product was purified to an oil (3.23 g) by a flash chromatography over silica

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

Procedure: 20 mmole of 3-mercapto-1H-1,2,4-triazole (potassium salt) was dissolved in 20 ml of ethanol in stirring. 10 mmole of 1,8-diiodooctane was added dropwise to the solution of 3-mercapto-1H-1,2,4-triazole (potassium salt), and stirred overnight. After the solvent was evaporated in vacuum, the residual was washed with 50 ml pure H2O for three times, and then with 50 ml hexane for 3 times. At last, the residual was dried in oven at 60° C. for 24 hours. 1.1 g product was obtained as white solid. Yield: 30%. 1H NMR (DMSO): δ(ppm) 8.34 (2H, s), 3.04 (4H, t, JH-H=7.14), 1.61 (4H, m), and 1.23-1.32 (8H, m). stirred overnight After the solvent was evaporated in vacuum the residual was washed with 50 ml pure H2O for three times At last, the residual was dried in oven at 60° C. for 24 hours

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

Procedure: 20 mmole of 5-mercapto-1H-1,2,3-triazole (sodium salt) was dissolved in 20 ml of ethanol in stirring. 10 mmole of 1,8-diiodooctane was added dropwise to the solution of 5-mercapto-1H-1,2,3-triazole (sodium salt), and stirred overnight. After the solvent was evaporated in vacuum, the residual was washed with 50 ml pure H2O for three times, and then with 50 ml hexane for 3 times. At last, the residual was dried in oven at 60° C. for 24 hours. 1.30 g product was obtained as white solid. Yield: 42%. 1H NMR (DMSO): δ (ppm) 7.88 (2H, s), 2.86 (4H, t, JH-H=7.14), 1.50 (4H, m), and 1.20-1.31 (8H, m). stirred overnight After the solvent was evaporated in vacuum the residual was washed with 50 ml pure H2O for three times At last, the residual was dried in oven at 60° C. for 24 hours

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

Procedure: 0.96 g (0.02 mol) of sodium hydride was added to 40 ml of dry tetrahydrofuran, and to this solution was added dropwise under reflux a mixed solution of 1.34 g (6 mmol) of ethyl diethylphosphonoacetate and 11 g (0.03 mol) of 1,8-diiodooctane, and the solution was refluxed under heating for 4 hours. After distilling off tetrahydrofuran, the residue was cooled to room temperature, added with 1N hydrochloric acid until the litmus paper came to show acidity of the solution and then extracted three times with 50 ml of ether. After drying the extract over anhydrous sodium sulfate, ether was distilled off and the obtained oily residue was refined by passing through a basic alumina(activity II)-packed column using benzene-ethyl acetate (2:1) as eluent to obtain 1.76 g of 2,2-bis(8-iodooctyl)-diethylphosphonoacetic acid ethyl ester, ##STR35## (yield: 42%). to this solution was added dropwise the solution was refluxed under heating for 4 hours After distilling off tetrahydrofuran added with 1N hydrochloric acid until the litmus paper extracted three times with 50 ml of ether After drying the extract over anhydrous sodium sulfate, ether was distilled off

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in an 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.05 (1H, d, C1-H), 8.77 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.35 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.68 (2H, t, C′1-CH2), 2.00 (2H, m, C′2-CH2), 1.30 (4H, m, C′3&4-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in an 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in an 89% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.07 (1H, d, C6-H), 5.09 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.25 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.5, 25.7. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in an 89% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diiodooctane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 93% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.11 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.59 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.28 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.6, 28.1, 25.2. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 93% yield