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Method for synthesizing acetyl substituted nitrogen heterocycle compounds

A technology of nitrogen heterocyclic compounds and synthesis methods, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problem of difficult recovery of organic amines or inorganic bases and environmental pollution , Difficulty in large-scale industrial production and other issues, to achieve the effect of less environmental pollution, easy operation and low cost

Inactive Publication Date: 2008-05-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the Heck reaction, the organic phosphine ligands and small molecule organic amines or inorganic bases used are difficult to recycle, and it is difficult to carry out large-scale industrial production, which also has certain pollution to the environment.

Method used

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  • Method for synthesizing acetyl substituted nitrogen heterocycle compounds
  • Method for synthesizing acetyl substituted nitrogen heterocycle compounds
  • Method for synthesizing acetyl substituted nitrogen heterocycle compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 prepares 2-acetylpyridine by 2-bromopyridine

[0024] 158 mg (1 mmol) of 2-bromopyridine, 200 mg (2 mmol) of n-butyl vinyl ether, 2.24 mg (0.01 mmol) of palladium acetate, 0.3 g (1.5 mmol) of Styrene-DVB (D301 R) resin mol), 50 milliliters of 1-methylpyrrolidone were placed in a 200 milliliter three-necked flask, stirred and heated, and reacted at 140° C. for 10 hours. Add hydrochloric acid to acidify to pH = 3, stir for 30 minutes, and extract three times with 50 ml of toluene. The extract is dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain 109 mg of the product, with a yield of 90%.

[0025] 1 HNMR (CDCl 3 )ppm: 2.73(s, 3H), 7.49(m, 1H), 7.84(m, 1H), 8.04(m, 1H), 8.69(d, 1H); 13 C NMR (CDCl 3 ) δppm: 26.1, 122.0, 127.4, 137.1, 149.2, 153.9, 200.4. MS (m / z): 121 (M + ).

Embodiment 2

[0026] Embodiment 2 prepares 3-acetylpyridine by 3-bromopyridine

[0027] 158 mg (1 mmol) of 3-bromopyridine, 200 mg (2 mmol) of n-butyl vinyl ether, 2.24 mg (0.01 mmol) of palladium acetate, 0.3 g (1.5 mmol) of Styrene-DVB (D301 T) resin mol), 50 ml of 1-methylpyrrolidone, placed in a 200 ml three-necked flask, stirred and heated, reacted at 100°C for 30 hours, cooled after the reaction, added hydrochloric acid to acidify to pH=3, stirred for 30 minutes, and used toluene Extracted three times with 50 ml of toluene, dried the extract with anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain 105.4 mg of the product with a yield of 86%.

[0028] 1 HNMR (CDCl 3 )ppm: 2.64(s, 3H), 7.35(m, 1H), 8.24(m, 1H), 8.78(m, 1H), 9.17(d, 1H); 13 C NMR (CDCl 3 ) δppm: 27.07, 124.0, 132.6, 135.8, 150.3, 153.9, 197.1. MS (m / z): 121 (M + ).

Embodiment 3

[0029] Embodiment 3 prepares 3-acetylpyridine by 3-chloropyridine

[0030] 114 mg (1 mmol) of 3-chloropyridine, 500 mg (5 mmol) of n-butyl vinyl ether, 2.24 mg (0.01 mmol) of palladium acetate, 0.4 g (1.5 mmol) of Styrene-DVB (D301G) resin ), 50 ml of dimethylformamide, placed in a 200 ml three-necked flask, stirred and heated, reacted at 140°C for 30 hours, cooled after the reaction, added hydrochloric acid to acidify to pH = 3, stirred for 30 minutes, and added 50 ml of toluene After extraction three times, the extract was dried with anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain 97 mg of product with a yield of 80%.

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Abstract

The present invention relates to the preparation method of acetyl-substituted nitrogen-containing heterocyclic compounds, in particular to a kind of macroporous weakly basic styrene-based anion-exchange resin as a solid base, using Heck reaction to prepare halogenated nitrogen-containing heterocyclic compounds and vinyl ether compounds Reaction to prepare acetyl-substituted nitrogen-containing heterocyclic compounds, halogenated nitrogen-containing heterocyclic compounds and vinyl ether compounds such as formula in an aprotic polar solvent, in the presence of palladium acetate and macroporous weakly basic styrene-based anion exchange resin , stirring and reacting at 60°C-180°C for 1-30 hours, acidifying the reaction liquid with acid to pH 1-3, separating and purifying the reaction liquid to obtain the product acetyl-substituted nitrogen-containing heterocyclic compounds. The technical scheme of the invention is novel in process, low in cost, easy to operate, and can be recycled and used after the reaction of the anion exchange resin is completed, and has little environmental pollution.

Description

(1) Technical field [0001] The invention relates to a preparation method of acetyl-substituted nitrogen-containing heterocyclic compounds, in particular to a method for using macroporous weakly basic styrene-based anion-exchange resin as a solid base and palladium acetate as a catalyst without using organic phosphine ligands and small-molecule organic compounds. Under the condition of amine or inorganic base, the Heck reaction is used to prepare acetyl-substituted nitrogen-containing heterocyclic compounds by reacting halogenated pyridines, pyrimidines or quinolines with vinyl ether compounds. (2) Background technology [0002] Acetyl-substituted nitrogen-containing heterocyclic compounds are important chemical raw materials and important intermediates of many drugs. Introduce acetyl group on the ring of nitrogen-containing heterocyclic compound, mainly use carboxyl derivative to directly carry out electrophilic acylation reaction under the catalysis of Lewis acid, and carry...

Claims

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Application Information

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IPC IPC(8): C07D213/50C07D215/14C07D239/26B01J31/06
Inventor 裴文吴香梅孙莉
Owner ZHEJIANG UNIV OF TECH
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