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Visible light induced polyfluoroalkyl aldehyde hydrazone derivative and synthesis method thereof

A technology of polyfluoroalkyl and aldehyde hydrazones, which is applied in the field of organic chemical synthesis, can solve the problems of high reaction temperature of stoichiometric free radical initiators, expensive transition metal catalysts, etc., and achieves environmental friendliness and good substrate universality , The effect of the simple operation of the reaction steps

Active Publication Date: 2019-08-30
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Abstract
  • Description
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Problems solved by technology

But such transformations usually rely on the use of expensive and toxic transition metal catalysts, strong oxidizing agents, toxic stoichiometric free radical initiators, or high reaction temperatures

Method used

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  • Visible light induced polyfluoroalkyl aldehyde hydrazone derivative and synthesis method thereof
  • Visible light induced polyfluoroalkyl aldehyde hydrazone derivative and synthesis method thereof
  • Visible light induced polyfluoroalkyl aldehyde hydrazone derivative and synthesis method thereof

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[0049] This embodiment provides a method for synthesizing polyfluoroalkylated aldehyde hydrazone derivatives induced by visible light. The synthesis steps are as follows:

[0050] Add aldehyde hydrazone, perfluoroalkane iodide, catalyst, base and solvent sequentially into the reactor, and react under visible light irradiation at room temperature with stirring;

[0051] After the reaction is completed, the solvent is adjusted with a rotary evaporator, and the crude product is obtained through column chromatography;

[0052] The catalyst is an organic dye.

[0053] Wherein, usually the above reaction process is under an inert gas (nitrogen or argon) environment, and the eluent used in the column chromatography is a mixed solvent of petroleum ether and ethyl acetate.

[0054] Its corresponding specific synthesis equation is as follows:

[0055]

[0056] After a lot of experimental verification: the perfluoroalkane iodide in the reactant can be a compound with C ≥ 1, for exam...

Embodiment 1

[0067]

[0068] The reactor was placed in nitrogen, and 0.2mmol (44.8mg) aldehyde hydrazone 1a, 0.3mmol (55.2mg) perfluoroiodobutane 2a, 5% (6.48mg) EY, 0.4mmol (55.2mg) K 2 CO 3 , 1mL DMA, under visible light irradiation, stirred at room temperature for 24h; after the reaction, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate to obtain 69.2mg of polyfluoroalkyl Aldehydrazone derivatives 3aa, the isolated yield was 82%.

[0069] see Figure 1 ~ Figure 3 , the characterization data of compound 3aa are as follows:

[0070] 1 H NMR (400MHz, CDCl 3 )δ7.40(d, J=8.4Hz, 2H), 7.31(d, J=8.0Hz, 2H), 3.62(t, J=4.8Hz, 4H), 3.01(t, J=4.8Hz, 4H) . 13 C NMR (100MHz, CDCl 3 )δ136.0, 133.7 (t, J=27.5Hz), 130.4, 130.1, 129.1, 65.9, 54.2. 19 F NMR (377MHz, CDCl 3 ) δ -81.1 (t, J = 9.6Hz, 3F), -106.7 (t, J = 12.3Hz, 2F), -120.1 (m, 2F), -124.5 (m, 2F)...

Embodiment 2

[0072]

[0073] The reactor was placed in nitrogen, and 0.2mmol (40.8mg) aldehyde hydrazone 1b, 0.3mmol (55.2mg) perfluoroiodobutane 2a, 5% (6.48mg) EY, 0.4mmol (55.2mg) K 2 CO 3 , 1mL DMA, under 18W visible light irradiation, stirred at room temperature for 24h; after the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate to obtain 43.1mg of polyfluoroalkane Aldehydrazone derivative 3ba was synthesized with an isolated yield of 51%.

[0074] see Figure 4 ~ Figure 6 , the characterization data of compound 3ba are as follows:

[0075] 1 H NMR (400MHz, CDCl 3 )δ7.26-7.31(m, 1H), 7.21(d, J=7.6Hz, 1H), 7.15(d, J=8.0Hz, 2H), 3.61(t, J=4.8Hz, 4H), 3.00( t,J=4.8Hz,4H),3.37(s,3H). 13 C NMR (100MHz, CDCl 3 )δ138.5, 135.3 (t, J=27.6Hz), 131.7, 130.5, 129.3, 128.6, 126.0, 66.0, 54.2, 21.4. 19 F NMR (377MHz, CDCl 3 ) δ -...

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Abstract

The invention discloses a visible light induced polyfluoroalkyl aldehyde hydrazone derivative and a synthesis method thereof. According to the polyfluoroalkyl aldehyde hydrazone derivative, an organicdye which is cheap and clean is adopted as a catalyst, and hydrazone and fluoroalkyl iodide are enabled to react with radiation of visible light, so that synthesis of the polyfluoroalkyl aldehyde hydrazone derivative is successfully achieved, and the polyfluoroalkyl aldehyde hydrazone derivative has the advantages of being good in substrate universality, simple in reaction step operation, low incatalyst cost, friendly to the environment, and the like.

Description

technical field [0001] The disclosure of the invention relates to the technical field of organic chemical synthesis, in particular to a visible light-induced polyfluoroalkylated aldehyde hydrazone derivative and a synthesis method thereof. Background technique [0002] Because of fluorine's unique position on the periodic table, past research and advances in modern chemistry have advanced the understanding of the structure, reactivity, and functional impact of fluorine-containing molecules. They often significantly alter the metabolic stability, lipophilicity, bioavailability and protein-ligand interactions of the corresponding bioactive molecules. Currently, about 30-40% of marketed agricultural chemicals and 25% of pharmaceuticals contain fluorine atoms. Although fluorine is one of the most abundant elements in the earth's crust, the presence of organofluorine compounds in nature is extremely rare, and only 13 fluorine-containing natural products have been isolated and ch...

Claims

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Application Information

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IPC IPC(8): C07D295/30C07D213/53
CPCC07D295/30C07D213/53
Inventor 李蕾王贺周明东彭振杨威
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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