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Phosphonated benzimidazoisoquinolone compounds as well as preparation method thereof

A technology of benzimidazole and isoquinolinone, which is applied in the field of preparation of phosphonylated benzimidazoloisoquinolinone compounds, can solve the problems that there are no literature reports on the preparation method, and achieve cheap and easy-to-obtain catalysts with high yield High, conducive to the effect of industrial production

Inactive Publication Date: 2019-08-02
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such phosphoryl-substituted benzimidazolo[2,1- a ] isoquinoline compound and preparation method thereof do not have bibliographical information at present

Method used

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  • Phosphonated benzimidazoisoquinolone compounds as well as preparation method thereof
  • Phosphonated benzimidazoisoquinolone compounds as well as preparation method thereof
  • Phosphonated benzimidazoisoquinolone compounds as well as preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of phosphonylated benzimidazolisoquinolinone compound, the steps are as follows:

[0023] Add N-methacryloyl-2-arylbenzimidazole (0.3 mmol), diphenylphosphine oxide (0.6 mmol), 2 mL of acetonitrile, potassium persulfate (0.6 mmol), silver nitrate in 8 mL reaction flask (0.06 mmol), stirred at 80°C for 12 h. After the reaction, the solvent was extracted, dried, and evaporated under reduced pressure. The residue was separated by silica gel column chromatography, and the yield of the final product was 78%.

[0024] The specific results are as follows:

[0025]

[0026] 1 H NMR (400 MHz, CDCl 3 ) δ 8.40 (dd, J = 7.9, 1.3 Hz, 1H), 8.30 (dd, J =7.3, 1.7 Hz, 1H), 7.80 (dd, J = 7.2, 1.5 Hz, 1H), 7.49 – 7.29 (m, 10H), 7.24– 7.11 (m, 5H), 3.86 (dd, J = 15.1, 10.3 Hz, 1H), 3.12 (dd, J = 15.1, 9.3 Hz,1H), 1.80 (d, J = 2.3 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.4 (d, J = 1.8Hz), 149.6, 143.9, 138.9 (d, J = 2.5 Hz), 133.2, 133.0, 132....

Embodiment 2

[0028] The preparation method of phosphonylated benzimidazolisoquinolinone compound, the steps are as follows:

[0029] Add N-methacryloyl-2-phenylbenzimidazole (0.3 mmol), bis(4-methylphenyl)phosphine oxide (0.6 mmol), 2 mL of acetonitrile, potassium persulfate (0.6 mmol), silver nitrate (0.06 mmol), stirred at 80°C for 12 h, after the reaction was completed, the solvent was extracted, dried, and evaporated under reduced pressure, and the residue was separated by silica gel column chromatography to obtain the final product with a yield of 66 %.

[0030] The specific results are as follows:

[0031]

[0032] 1 H NMR (400 MHz, CDCl 3 ) δ 8.38 (dd, J = 7.9, 1.4 Hz, 1H), 8.23 ​​– 8.21 (m,1H), 7.80 – 7.75 (m, 1H), 7.46 – 7.34 (m, 6H), 7.29 – 7.25 (m, 1H), 7.21 –7.12 (m , 4H), 6.81 (dd, J = 8.1, 2.7 Hz, 2H), 3.77 (dd, J = 15.2, 8.9 Hz,1H), 3.06 (dd, J = 15.2, 11.5 Hz, 1H), 2.34 (s, 3H), 1.93 (s, 3H), 1.73 (d, J = 2.4 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.3 (d...

Embodiment 3

[0034] The preparation method of phosphonylated benzimidazolisoquinolinone compound, the steps are as follows:

[0035] Add N-methacryloyl-2-phenylbenzimidazole (0.3 mmol), bis(4-chlorophenyl)phosphine oxide (0.6 mmol), 2 mL of acetonitrile, potassium persulfate (0.6 mmol), silver nitrate (0.06 mmol), stirred at 80°C for 12h, after the reaction was finished, extracted, dried, and evaporated the solvent under reduced pressure, and the residue was separated by silica gel column chromatography, and the yield of the final product was 77%. .

[0036] The specific results are as follows:

[0037]

[0038] 1 H NMR (400 MHz, CDCl 3 ) δ 8.41 (d, J = 7.4 Hz, 1H), 8.29 – 8.25 (m, 1H),7.84 – 7.80 (m, 1H), 7.45 – 7.27 (m, 9H), 7.21 – 7.13 (m, 4H), 3.77 (dd, J =15.1, 10.2 Hz, 1H), 3.05 (dd, J = 15.1, 9.4 Hz, 1H), 1.79 (d, J = 2.4 Hz,3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.1 (d, J = 1.9 Hz), 149.4, 143.9, 138.7 (dd, J = 5.7, 2.9 Hz), 138.2 (d, J = 3.5 Hz), 132.0, 131.9 (...

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Abstract

The invention discloses phosphonated benzimidazoisoquinolone compounds as well as a preparation method thereof. According to the compounds, N-methacryloyl-2-aryl benzimidazole compounds and diaryl phosphine oxygen are used as raw materials, and the phosphonated benzimidazoisoquinolone compounds are synthesized under the action of silver nitrate and potassium persulfate. The method has the advantages that the raw materials are low in price and easy to obtain, the reaction conditions are mild, the operation is simple and prone to enlarge, and industrial production and application prospects are provided. The compounds have potential application value in the research fields such as medicines / organic synthesis and the like, and the invention provides a new method for the synthesis of the phosphonated benzimidazoisoquinolone compounds.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing phosphonylated benzimidazoloisoquinolinone compounds. Background technique [0002] Benzimidazole-isoquinolinone derivatives, such as benzimidazole-isoquinoline-6(5 H )-ketone is an important heterocyclic skeleton. Due to its important chemical and biological activities, benzimidazole-isoquinoline-6 ​​(5 H )-ketone derivatives show good application potential in anti-diabetic, anti-inflammatory and anti-tumor aspects. Therefore, it is of great significance to develop efficient methods to synthesize novel benzimidazoloisoquinolinone derivatives. Organophosphorus compounds are not only ubiquitous in medicinal chemistry but also exhibit important functions in materials science and organic synthesis. The introduction of phosphorus-containing functional groups can alter drug properties and biological responses as well as effective selection of substance func...

Claims

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Application Information

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IPC IPC(8): C07F9/6561
CPCC07F9/6561
Inventor 陈晓岚司亚峰於兵屈凌波
Owner ZHENGZHOU UNIV
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