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Uses of 2-pyridine-beta ketone compounds

A technology of ketone compounds and pyridine, which is applied in the field of chemistry, can solve the problems of expensive palladium reagents and difficult substrate reactions, etc., and achieve the effect of novelty, cheap price and good application prospects of 2-pyridine-β-ketone compounds

Active Publication Date: 2009-04-08
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still many limitations in the use of palladium catalysts, such as substrates containing certain functional groups are difficult to react, and palladium reagents are expensive

Method used

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  • Uses of 2-pyridine-beta ketone compounds
  • Uses of 2-pyridine-beta ketone compounds
  • Uses of 2-pyridine-beta ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Ligand 2-Enteropyridine

[0034]

[0035]Under the protection of argon, add 2.96ml (32mmol) 2-picoline dropwise to 60ml THF solution dissolved with 32mmol nBuLi at 0°C, stir and react at 0°C for 45min, add 1.56ml (32mmol) acetonitrile to the reaction mixture, and stir at room temperature 3h, add 30ml*3N sulfuric acid to the reaction mixture, extract the ionic phase with diethyl ether (2*25ml), then basify with 2N sodium hydroxide solution (PH=11~12), extract with dichloromethane, and extract the organic phase with Dry over sodium sulfate, spin off the solvent under reduced pressure, and then distill the remaining oil under reduced pressure to obtain 2.2 g of the product (yield: 51%).

[0036] 1 H NMR (CDCl 3 ): δ=8.52(d, J=4.8Hz, 1H; Phenyl), 7.60(td, J=8.0, 1.6Hz, 1H; Phenyl), 7.20-7.15(m, 2H; Phenyl), 3.89(s, 2H ;CH 2 ), 2.19ppm (s, 3H; CH 3 ); 13 C NMR (CDCl 3 ): δ=205.3 (-C=O), 154.7, 149.5, 136.7, 124.1, 121.9 (Phenyl), 53.1 (CH 2 ), 29.9ppm...

Embodiment 2

[0038] Synthesis of Ligand 2-(isobutyrylmethyl)pyridine

[0039]

[0040] Synthesis method as in Example 1, yield: 50%.

[0041] 1 H NMR (CDCl 3 ): δ=8.52(d, J=4.8Hz, 1H; Phenyl), 7.60(td, J=7.6, 1.6Hz, 1H; Phenyl), 7.21-7.13(m, 2H; Phenyl), 3.96(s, 2H ;CH 2 ), 2.80-2.74 (m, 1H; CH), 1.11ppm (d, J=7.2Hz, 6H; 2CH 3 ); 13 C NMR (CDCl 3 ): δ=211.1 (-C=O), 155.1, 149.4, 136.5, 124.2, 121.9 (Phenyl), 49.9 (CH 2 ), 40.8(CH), 18.1ppm(CH 3 ); GC / MS: rt=5.91min, M / Z=163.

Embodiment 3

[0043] Synthesis of Ligand 8-Acetyl-5,6,7,8-Tetrahydroquinoline

[0044] Under the protection of argon, 4.26g (32mmol) 5,6,7,8-tetrahydroquinoline was added dropwise to 60ml THF solution dissolved with 32mmol nBuLi at 0°C, stirred at 0°C for 45min, and 1.56ml was added to the reaction mixture (32mmol) acetonitrile, stirred at room temperature for 3h, added 30ml*3N sulfuric acid to the reaction mixture, extracted the ionic phase with diethyl ether (2*25ml), then basified with 2N sodium hydroxide solution (PH=11~12), washed with dichloro Extract with methane, dry the organic phase with anhydrous sodium sulfate, spin off the solvent under reduced pressure, and distill the remaining oil under reduced pressure to obtain 2.3 g of the product, yield: 46%.

[0045]

[0046] 1 H NMR (CDCl 3 ): δ=8.41(s, 1H; Phenyl), 7.42(d, J=7.6Hz, 1H; Phenyl), 7.09(t, J=7.2Hz, 1H; Phenyl), 4.01(t, J=6.4Hz, 1H; CH), 2.882-2.78 (m, 2H; CH 2 ), 2.25(s, 3H; CH 3 ), 2.16-2.12 (m, 2H; CH 2 ), 1.81...

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Abstract

The invention relates to application of a 2-pyridyl-beta ketone compound taking a structure of formula I as an additive in the process of promoting N-arylation reaction. In the invention, because the 2-pyridyl-beta ketone compound is used as the additive, the N-arylation reaction can be promoted well, and the catalyst used in the N-arylation reaction is just CuI which is cheap and available; and the additive 2-pyridyl-beta ketone compound is novel and is stable in air; compared with the same type of reaction reported in a literature, the ullmann reaction of iodo compounds can be performed at room temperature, and the temperature of a bromo compound reaction can be reduced by about 20 DEG C on average, thus the reaction condition is very mild and the application prospect is good.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to the application of 2-pyridine-β-ketone compounds. Background technique [0002] The Ullmann coupling reaction (Ullmann, F.ber Dtsch.Chem.Ges.1903, 36, 2382.) has a long history of development, has attracted widespread attention academically, and the reaction has been realized in industrial production (Lindley, J. Tetrahedron 1984, 40, 1433). Traditional Ullmann coupling reaction is owing to require to carry out under high temperature, highly polar solvent condition, and needs a large amount of copper reagents, thereby makes the application of this reaction be subjected to very big restriction (Lindley, J.Tetrahedron 1984,40, 1433). In recent years palladium catalysts ((a) Yang, B.H.; Buchwald, S.L.J.Organomet.Chem.1999, 576(1-2), 125-146. (b) Hartwig, J.F.Angew.Chem., Int.Ed.Engl. 1998, 37, 2046-2067), the conditions for this reaction to be carried out have been greatly im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/04B01J31/02B01J31/30
Inventor 丁克王德平
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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