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A kind of synthetic method of gem-difluoro substituted pyrrolidone compound

A technology of pyrrolidone and synthesis method, applied in directions such as organic chemistry, to achieve the effects of wide substrate range, simple operation and high yield

Active Publication Date: 2019-08-30
ANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, the method of synthesizing gem-difluoro-substituted pyrrolidone compounds through the reaction of alkenes with bromodifluoroacetamides and using cheap and easy-to-obtain copper salts as catalysts has not been reported in the literature.

Method used

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  • A kind of synthetic method of gem-difluoro substituted pyrrolidone compound
  • A kind of synthetic method of gem-difluoro substituted pyrrolidone compound
  • A kind of synthetic method of gem-difluoro substituted pyrrolidone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Into a 35 ml sealed tube equipped with a stir bar, add 79.2 mg (0.3 mmol) of bromodifluoroacetyl-p-toluidine, 3.0 ml of acetonitrile, and 41 μL of styrene (0.36 mmol), and mix well. Then add 5.4 mg Phen (0.03 mmol), 5.7 mg CuI (0.03 mmol) and 82.9 mg K 2 CO 3 (0. 6 mmol). The mouth of the tube was sealed, and the reaction was stirred at 110°C for 2 hours (the progress of the reaction was monitored by TLC). After the reaction is over, cool to room temperature, add 3ml of distilled water to the reaction mixture, extract with ethyl acetate (5ml×3), combine the organic phases, dry with anhydrous sodium sulfate, distill under reduced pressure to remove the solvent, and the residue is subjected to silica gel column chromatography (V Petroleum ether : V Ethyl acetate =30:1) 74.8 mg of white solid product 3a was isolated, with a yield of 87%. The response is as follows:

[0025]

[0026] Spectral analysis data

[0027] White solid. mp: 139-140 ºC. 1 H NMR (400 MHz, CDCl 3 ): δ...

Embodiment 2

[0029] Into a 35 ml sealed tube equipped with a stir bar, add 79.2 mg (0.3 mmol) of bromodifluoroacetyl-p-toluidine, 3.0 ml of acetonitrile, and 53.6 mg of 4-nitrostyrene (0.36 mmol), and mix well. Then add 5.4 mg Phen (0.03 mmol), 5.7 mg CuI (0.03 mmol) and 82.9 mg K 2 CO 3 (0. 6 mmol). The mouth of the tube was sealed, and the reaction was stirred at 110°C for 2 hours (the progress of the reaction was monitored by TLC). After the reaction is complete, cool to room temperature, add 3 ml of distilled water to the reaction mixture, extract with ethyl acetate (5 ml×3), combine the organic phases, dry with anhydrous sodium sulfate, distill under reduced pressure to remove the solvent, and pass the residue through a silica gel column Analysis (V Petroleum ether : V Ethyl acetate =30:1) 91.7 mg of white solid product 3b was isolated, and the yield was 92%. The response is as follows:

[0030]

[0031] Spectral analysis data

[0032] White solid. mp: 144-146 ºC. 1 H NMR (400 MHz, CD...

Embodiment 3

[0034] Into a 35 ml sealed tube equipped with a stir bar, add 79.2 mg (0.3 mmol) of bromodifluoroacetyl-p-toluidine, 3.0 ml acetonitrile, and 62 μL eugenol methyl ether (0.36 mmol), and mix well. Then add 5.4 mg Phen (0.03 mmol), 5.7 mg CuI (0.03 mmol) and 82.9 mg K 2 CO 3 (0. 6 mmol). The mouth of the tube was sealed, and the reaction was stirred at 110°C for 2 hours (the progress of the reaction was monitored by TLC). After the reaction is complete, cool to room temperature, add 3 ml of distilled water to the reaction mixture, extract with ethyl acetate (5 ml×3), combine the organic phases, dry with anhydrous sodium sulfate, distill under reduced pressure to remove the solvent, and pass the residue through a silica gel column Analysis (V Petroleum ether : V Ethyl acetate =30:1) 99.7 mg of white solid product 3c was isolated, with a yield of 60%. The response is as follows:

[0035]

[0036] Spectral analysis data

[0037] White solid. mp: 135-136 ºC. 1 H NMR (400 MHz, CDCl 3...

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Abstract

The invention specifically discloses a synthetic method for a gem-difluoro-substituted pyrrolidone compound, belonging to the technical field of organic synthetic chemistry. The synthetic method comprises the following steps: dissolving a bromodifluoroacetyl amine compound in a solvent, adding olefin and carrying out uniform mixing; then adding ligand phenanthroline, a catalyst CuI and alkali K2CO3, carrying out heating to 110 + / - 10 DEG C under en enclosed condition and carrying out a stirring reaction for 1 to 3 h; and carrying out after-treatment after completion of the reaction so as to obtain the gem-difluoro-substituted pyrrolidone compound. The synthetic method provided by the invention overcomes the defect of tedious steps in synthesis of the gem-difluoro-substituted pyrrolidone compound via multi-step reactions in the prior art, has the characteristics of good atom economy, simple reaction steps, usage of cheap and easily available raw materials, a wide substrate application scope, etc., and is applicable to synthesis of a variety of gem-difluoro-substituted pyrrolidone compounds and suitable for industrial production.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of chemical organic synthesis, and specifically relates to a method for catalytically synthesizing geminal difluoro-substituted pyrrolidone compounds by using olefins and brominated difluoroacetamide compounds as raw materials. [0003] Background technique: [0004] Nitrogen-containing heterocyclic compounds are widely used in the fields of medicine, agrochemicals and materials. The introduction of fluorine atoms or fluorine-containing molecules can improve their lipophilicity and metabolic stability, and improve the efficacy of biomedicine ((a) Uneyama, K.; Sasaki , K.Pharmaceuticals containing fluorinated heterocyclic compounds. In Fluorinated Heterocyclic Compounds: Synthesis, Chemistry and Application ; Petrov, V. A., Ed.; John Wiley & Sons: Hoboken, 2009; 419. (b) Nosova, E. V.; Lipunova, G.N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem . 2010, 131 , 1267.). Among them, compounds with pyrro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/273
Inventor 吕允贺蒲卫亚孙凯李刚张前
Owner ANYANG NORMAL UNIV
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