Iron catalyst system for preparation of pyridine derivatives and its application
A technology for iron catalysts and derivatives, which is applied in the field of iron catalysts for the preparation of pyridine derivatives, can solve the problems of slow development of catalytic systems, restrictions on the application of iron catalytic systems, and difficulty in preparation, and achieves simple and practical reaction operations, high yields, Easy to prepare
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[0020] Example 1: Preparation and screening of iron catalyst
[0021] The iron metal precursor (0.05 mmol) and the bisphosphine ligand (0.10 mmol) were added to the reaction flask, and after argon replacement, 1 mL of tetrahydrofuran was added, and the mixture was stirred at room temperature for 0.5 hours. Then add the reducing agent Zn (0.10 mmol) and stir, then add the diacetylene 1a (0.25 mmol) and the nitrile 2a (2.5 mmol), and react at room temperature for 24 hours. After the reaction, the solvent was removed, and the pure product was obtained by direct column chromatography. The structure was confirmed by nuclear magnetism. The reaction formula and ligand structure are shown in formula 4:
[0022]
[0023] The conversion and yield were determined by gas chromatography (internal standard method), and some of the results are listed in Table 1:
[0024] Table 1. Screening of iron catalyst
[0025]
Example Embodiment
[0026] Example 2: Synthesis of pyridine derivatives by iron-catalyzed [2+2+2] cycloaddition reaction of diacetylene and nitrile
[0027] Add FeI to the reaction flask 2 (0.05mmol) and dppp (0.10mmol). After argon replacement, 2mL of tetrahydrofuran was added and stirred at room temperature for 0.5 hours. Then the reducing agent Zn (0.10 mmol), diyne 1 (0.5 mmol) and nitrile 2 (2.5 mmol) were added, and the reaction was stirred at room temperature for 24 hours. After the reaction, the solvent was removed, and the pure product 3 was obtained by direct column chromatography. The structure was confirmed by nuclear magnetism. The reaction formula and the yield of some products are shown in formula 5:
[0028] The NMR data of some products are as follows:
[0029] 3a: 1 H NMR (400MHz, Acetone) δ 7.57-7.30 (m, 5H), 3.76 (s, 6H), 3.62 (s, 2H), 3.61 (s, 2H), 2.40 (s, 3H), 2.23 (s, 3H); 13 C NMR (100MHz, Acetone) δ 172.4, 157.2, 151.0, 150.3, 141.9, 133.3, 130.1, 128.6, 128.2, 124.8, 60.1, 5...
Example Embodiment
[0034] Example 3: Synthesis of pyridine derivatives by iron-catalyzed [2+2+2] cycloaddition reaction of monoacetylene and nitrile
[0035] Add FeI to the reaction flask 2 (0.05mmol) and dppp (0.10mmol). After argon replacement, 2mL of tetrahydrofuran was added and stirred at room temperature for 0.5 hours. Then the reducing agent Zn (0.10 mmol), monoacetylene 4 (1 mmol) and nitrile 2 (2.5 mmol) were added, and the reaction was stirred at room temperature for 24 hours. After the reaction, the solvent was removed, and the pure products 5 and 6 were obtained by direct column chromatography. The structure was confirmed by nuclear magnetism. The reaction formula and the yield of some products are shown in formula 6:
[0036]
[0037] The NMR data of some compounds are as follows:
[0038] 5: 1 H NMR (500MHz, Acetone) δ 8.18 (dt, J = 8.3, 1.7 Hz, 2H), 7.83 (d, J = 7.9 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.53-7.47 (m, 4H), 7.47-7.40 (m, 4H), 2.54 (s, 3H); 13 C NMR (125MHz, Acetone) δ 156.1...
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