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Preparation method of 2-phosphonothioflavone compound

A technology of phosphonothioflavones and compounds, which is applied in the field of aqueous phase photocatalytic preparation of 2-phosphonothioflavones, can solve problems such as high reaction temperature, achieve great application value, and achieve the effect of rapid and efficient construction

Active Publication Date: 2020-03-24
XINYANG AGRI & FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the construction of carbon-phosphorus bonds has been widely concerned by the academic community in the past few decades. At present, the construction of carbon-phosphorus bonds mainly relies on traditional cross-coupling reactions and free radical tandem cyclization reactions that have emerged in recent years, but These reactions often require the use of peroxides, transition metals (manganese, silver, copper, iron, ruthenium, iridium, etc.) and higher reaction temperatures, thus limiting their practical applications

Method used

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  • Preparation method of 2-phosphonothioflavone compound
  • Preparation method of 2-phosphonothioflavone compound
  • Preparation method of 2-phosphonothioflavone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The preparation method of phosphonothioflavone compound 1, the steps are as follows:

[0025] In a 10mL reaction flask, add 2-methylthiophenylpropynone (0.2mmol), diphenylphosphine oxide (0.4mmol), lauryl peroxide (2.0 equivalents), tetracarbazole-dibenzonitrile (5mol %), then 2.5mL water was added to the reaction system, the reaction bottle was sealed after feeding nitrogen, and stirred at room temperature for 24 hours under the irradiation of a white light-emitting diode, until 2-methylthiophenylpropynylketone was completely converted, and The reaction solution was extracted with ethyl acetate (3×5 mL), the organic phases were combined, and dried over anhydrous and sodium sulfate, and the organic solvent was spun off. The crude product was purified by silica gel column chromatography to obtain 2-phosphonothioflavone product 1.

[0026] The specific results are as follows:

[0027]

[0028] 1 H NMR (400MHz, Chloroform-d) δ8.23 (dd, J=8.1, 1.1Hz, 1H), 7.78-7.72(m, ...

Embodiment 2

[0030] The preparation method of phosphonothioflavone compound 2, the steps are as follows:

[0031] Add 2-methylthiophenylpropynone (0.2mmol), diphenylphosphine oxide (0.4mmol), lauryl peroxide (2.0 equivalents), and tetracarbazole m-dibenzonitrile (5mol) in a 10mL reaction flask. %), then 2.5mL water was added to the reaction system, the reaction bottle was sealed after feeding nitrogen, and stirred at room temperature for 24 hours under the irradiation of a white light-emitting diode, until 2-methylthiophenylpropynylketone was completely converted, and The reaction solution was extracted with ethyl acetate (3×5 mL), the organic phases were combined, and dried over anhydrous and sodium sulfate, and the organic solvent was spun off. The crude product was purified by silica gel column chromatography to obtain 2-phosphonothioflavone product 2.

[0032] The specific results are as follows:

[0033]

[0034] 1 H NMR (400MHz, Chloroform-d) δ8.23 (dd, J = 8.1, 1.4Hz, 1H), 7.81...

Embodiment 3

[0036] The preparation method of phosphonothioflavone compound 3, the steps are as follows:

[0037] In a 10mL reaction flask, add 2-methylthiophenylpropynone (0.2mmol), diphenylphosphine oxide (0.4mmol), lauryl peroxide (2.0 equivalents), tetracarbazole-dibenzonitrile (5mol %), then 2.5mL water was added to the reaction system, the reaction bottle was sealed after feeding nitrogen, and stirred at room temperature for 24 hours under the irradiation of a white light-emitting diode, until 2-methylthiophenylpropynone was completely converted, and The reaction solution was extracted with ethyl acetate (3×5 mL), the organic phases were combined, and dried over anhydrous and sodium sulfate, and the organic solvent was spun off. The crude product was purified by silica gel column chromatography to obtain 2-phosphonothioflavone product 3.

[0038] The specific results are as follows:

[0039]

[0040] 1 H NMR (400MHz, Chloroform-d) δ8.21 (dd, J = 8.1, 1.3Hz, 1H), 7.77-7.72 (m, 4H...

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Abstract

The invention discloses a preparation method of a 2-phosphonothioflavone compound, which is a method for synthesizing the 2-phosphonothioflavone compound by utilizing water phase visible light catalysis. According to the invention, tetrazole m-dibenzonitrile (4-CzIPN) is used as a photosensitizer, lauroyl peroxide is used as an oxidizing agent, 2-methylthiophenyl propynone and diarylphosphine oxide are used as initial raw materials, water is used as a solvent, and under the protection of nitrogen, an illumination reaction is carried out at room temperature for 24 hours to obtain a target product. The invention provides a method for preparing the 2-phosphonothioflavone compound through water-phase photocatalysis of radical series cyclization reaction for the first time. Compared with a traditional method, according to the method, traditional precious metal (such as ruthenium and iridium) organic photosensitizers do not need to be used, the 2-phosphonothioflavone compound is rapidly andefficiently synthesized under the extremely mild and environment-friendly reaction condition, and the method has huge potential application value in the fields of environment-friendly synthetic chemistry, heterocyclic compound construction through photocatalytic reaction and pharmaceutical and chemical engineering.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a water-phase photocatalytic preparation method of 2-phosphonothioflavonoids. Background technique [0002] Scientific researchers in various fields pay more and more attention to how to minimize the impact of research behavior on the environment to ensure sustainable development. Especially for organic chemistry, the development of environmentally friendly and green and sustainable synthetic methods is the only way for the development of organic chemistry. One of the adverse effects of classical organic synthesis on the environment is the use of organic solvents. Since chemical reactions often require heating, organic solvent liquids or vapors may cause dangers such as violent combustion or even explosions under these conditions, thereby causing corresponding safety and pollution problems. Such accidents are common. For this reason, the academic community put forward ...

Claims

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Application Information

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IPC IPC(8): C07F9/6553
CPCC07F9/655372
Inventor 商天奕刘琰陈重潘岩杨俊杰刘晓层孙凯於兵
Owner XINYANG AGRI & FORESTRY UNIV
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