1,10-diiododecane

反応条件: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of butyllithium (2.84 ml of a 1.6 M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At his temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 91% 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), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-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, 28.9, 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 a 91% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 91% 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), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-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, 28.9, 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 a 91% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 90% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.10 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.60 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.24 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.6, 30.6, 28.8, 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 90% yield

反応条件: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of butyllithium (2.84 ml of a 1.6M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At this temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

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

実験手順: The title compound is prepared from 4-benzyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 1,10-diiododecane according to the procedure of Example 5.

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

実験手順: The title compound is prepared from 4-benzyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 1,10-diiododecane according to the procedure of Example 5.

反応条件: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of butyllithium (2.84 ml of a 1.6 M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At his temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,10-Diiododecane (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 a 91% 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), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-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, 28.9, 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 a 91% yield