A kind of preparation method of N-(aryl/heteroaryl) alkyl-diamide
A diamide and heteroaryl technology, which is applied in the field of organic chemical synthesis, can solve the problems of rising synthesis cost, low step economy, limitation of substrate adaptability, etc., and achieves reduction of synthesis cost, clean reaction process, and substrate adaptability. wide range of effects
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Embodiment 1
[0025] Example 1 The preparation of 1-(quinoline-2-methyl)pyrrolidine-2,5-dione 1, the synthesis route is as follows:
[0026]
[0027] Under nitrogen protection, N-bromosuccinimide B1 (1.25 mmol), CuI (0.025 mmol), PPh 3 (0.05 mmol), AIBN (0.05 mmol), potassium carbonate (1.0 mmol), quinaldine A1 (0.5 mmol) and 1,4-dioxane (2 mL) were added to the reaction tube. Stir at 120°C for 24 hours, stop the reaction, cool to room temperature, evaporate the solvent to dryness, and separate by column chromatography. The volume ratio of the eluent used (mL / mL) is ethyl acetate:petroleum ether=1:10 ~ 1:1 , to obtain 1-(quinoline-2-methyl)pyrrolidine-2,5-dione 1 with a yield of 84%.
[0028] 1-(quinoline-2-methyl)pyrrolidine-2,5-dione 1: 1 H NMR (400 MHz, CDCl 3 ) δ 8.07 (d, J = 8.5 Hz, 1H), 7.99 (d, J = 8.5 Hz, 1H), 7.74 (d, J = 8.1 Hz, 1H), 7.65 (t, J = 8.4 Hz, 1H), 7.48 (t, J = 8.9 Hz, 1H), 7.30 (d, J = 8.7 Hz, 1H), 4.99 (s,2H), 2.81 (s, 4H), 13 C NMR (100 MHz, CDCl 3...
Embodiment 2
[0029] Example 2 The preparation of 1-(6-methylquinoline-2-methyl)-pyrrolidine 2,5-dione 2, its synthetic route is as follows:
[0030]
[0031] Under nitrogen protection, N-bromosuccinimide B1 (1.25 mmol), CuI (0.025 mmol), PPh 3 (0.05 mmol), AIBN (0.05 mmol), potassium carbonate (1.0 mmol), 2,6-dimethylquinoline A2 (0.5 mmol) and 1,4-dioxane (2 mL) were added to the reaction tube. Stir at 120°C for 24 hours, stop the reaction, cool to room temperature, evaporate the solvent to dryness, and separate by column chromatography. The volume ratio of the eluent used (mL / mL) is ethyl acetate:petroleum ether=1:10 ~ 1:1 , to obtain 1-(quinoline-2-methyl)pyrrolidine-2,5-dione 2 with a yield of 70%.
[0032] 1-(6-Methylquinoline-2-methyl)pyrrolidine-2,5-dione 2: 1 H NMR (400 MHz, CDCl 3 ) δ 7.91(d, J = 8.4 Hz, 1H), 7.80 (d, J = 8.5 Hz, 1H), 7.43-7.40 (m, 2H), 7.20-7.18(m, 1H), 4.90 (s, 2H), 2.75 (s, 4H), 2.42 (s, 3H), 13 C NMR (100 MHz, CDCl 3 ) δ 177.21, 153.50, 146.25...
Embodiment 3
[0033] Example 3 Preparation of 1-(6-fluoroquinoline-2-methyl)pyrrolidine-2,5-dione 3, the synthetic route is as follows:
[0034]
[0035] Under nitrogen protection, N-bromosuccinimide B1 (1.25 mmol), CuI (0.025 mmol), PPh 3 (0.05 mmol), AIBN (0.05 mmol), potassium carbonate (1.0 mmol), 2-methyl-6-fluoroquinoline A3 (0.5 mmol) and 1,4-dioxane (2 mL) were added to the reaction tube . Stir at 120°C for 24 hours, stop the reaction, cool to room temperature, evaporate the solvent to dryness, and separate by column chromatography. The volume ratio of the eluent used (mL / mL) is ethyl acetate:petroleum ether=1:10 ~ 1:1 , to obtain 1-(6-fluoroquinoline-2-methyl)pyrrolidine-2,5-dione 3 with a yield of 53%.
[0036] 1-(6-fluoroquinoline-2-methyl)pyrrolidine-2,5-dione 3: 1 H NMR (400 MHz, CDCl 3 ) δ 8.05(d, J = 8.4 Hz, 1H), 7.98 (dd, J = 9.24 Hz, 5.4 Hz, 1H), 7.46-7.34 (m, 3H),4.99 (s, 2H), 2.86 (s, 4H), 13 C NMR (100 MHz, CDCl 3 ) δ 177.15, 161.60, 159.13, 153.76 (d, ...
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