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Synthesis method of 1, 2-dione derivatives

A synthesis method and a technology of derivatives, which are applied in the fields of oxidative preparation of carbonyl compounds, preparation of sulfonic acid amides, organic chemistry, etc., to achieve the effects of high yield, easy availability of raw materials, and mild reaction conditions

Active Publication Date: 2015-09-09
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the synthesis method of diketone derivatives, the method of synthesizing 1,2-diketone derivatives by oxidation method using cheap and environmentally friendly metal zinc salts as catalysts and starting from simple and easy-to-obtain alkynes has not been reported yet.

Method used

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  • Synthesis method of 1, 2-dione derivatives
  • Synthesis method of 1, 2-dione derivatives
  • Synthesis method of 1, 2-dione derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of diphenyl ketone, its structural formula is:

[0025]

[0026] Preparation method 1: In a reaction tube, 12.8 mg of zinc iodide, 35.6 mg of toluene, 71.4 mg of sodium persulfate and 2.0 mL of dimethyl sulfoxide were added under nitrogen protection. Place it in an oil bath at 120°C for 24 hours. Conventional treatment yielded 32.4 mg of pure product with a yield of 77%.

[0027] Preparation method 2: In a reaction tube, add 12.8 mg of zinc iodide, 35.6 mg of toluene, 71.4 mg of sodium persulfate and 2.0 mL of dimethyl sulfoxide under nitrogen protection. Place it in an oil bath at 110°C for 24 hours. Conventional treatment yielded 22.3 mg of pure product with a yield of 53%.

[0028] Preparation method 3: In a reaction tube, add 12.8 mg of zinc iodide, 35.6 mg of toluene, 71.4 mg of sodium persulfate and 2.0 mL of dimethyl sulfoxide in an air atmosphere. Place it in an oil bath at 120°C for 24 hours. Conventional treatment yielded 31.5 mg of pure ...

Embodiment 2

[0035] Synthesis of 1-phenyl-2-(4-methylphenyl)-1,2,-dione, whose structural formula is:

[0036]

[0037] In a reaction tube, 12.8 mg of zinc iodide, 38.5 mg of 1-phenyl-2-(4-methylphenyl)acetylene, 71.4 mg of sodium persulfate and 2.0 mL of dimethyl sulfoxide were added under nitrogen protection. Place it in an oil bath at 120°C for 24 hours. Conventional treatment yielded 27.4 mg of pure product with a yield of 61%.

[0038] The result of NMR characterization of the product is: 1 H NMR (400MHz, CDCl 3 )δ7.97(dd, J=10.8,3.5Hz,2H),7.87(d,J=8.1Hz,2H),7.65(t,J=7.4Hz,1H),7.50(t,J=7.7Hz, 2H), 7.31(d, J=8.0Hz, 2H), 2.43(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ 22.04, 129.10, 129.14, 129.86, 130.00, 130.14, 130.71, 133.22, 134.90, 146.34, 194.42, 194.89.

Embodiment 3

[0040] Synthesis of 1-(4-methoxyphenyl)-2-phenyl-1,2,-dione, whose structural formula is:

[0041]

[0042] In the reaction tube, 12.8 mg of zinc iodide, 41.7 mg of 1-(4-methoxyphenyl)-2-phenylacetylene, 71.4 mg of sodium persulfate and 2.0 mL of dimethyl sulfoxide were added under nitrogen protection. Place it in an oil bath at 120°C for 24 hours. Conventional treatment yielded 41.8 mg of pure product with a yield of 87%.

[0043] The result of NMR characterization of the product is: 1 H NMR (400MHz, CDCl 3 )δ8.00-7.92 (m, 4H), 7.64 (t, J = 7.4Hz, 1H), 7.50 (t, J = 7.9Hz, 2H), 6.97 (d, J = 9.0Hz, 2H), 3.88 ( s,3H); 13 C NMR (100MHz, CDCl 3 )δ55.76, 114.49, 126.20, 129.06, 129.99, 132.48, 133.31, 134.82, 165.11, 193.28, 194.97.

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Abstract

The invention discloses a synthesis method of 1, 2-dione derivatives by utilizing polyacetylenes. According to the method, in a nitrogen environment, polyacetylenes, an oxidant and an organic solvent are mixed up under the presence of zinc salt as a catalyst, and then heated to react with one another to obtain1, 2-dione derivatives. The substrate of the method is wide in compatibility, mild in condition and high in synthesis yield. The metal zinc salt adopted as the catalyst is low in price and environmentally-friendly. Easily available polyacetylenes are adopted as the substrate of the method, so that the method has the advantages of low cost, high yield, simple operation, readily available raw materials and easy industrial production.

Description

technical field [0001] The invention relates to the synthesis of a class of diketone derivatives, in particular to a method for realizing the synthesis of 1,2-diketone derivatives through the oxidation reaction of alkynes. Background technique [0002] Diketone derivatives are an important structural template in the field of chemical synthesis, and many molecules with physiological and biological activities have this type of structure. This type of compound can be used as an important synthetic module in the fields of organic synthesis and pharmaceuticals, and can be used to construct important heterocyclic molecules such as quinoxaline and imidazole. [0003] At present, a large number of literatures have reported various synthetic strategies and reaction systems applied to the synthesis of 1,2-diketone derivatives. The most direct method is to realize the preparation of such derivatives through the selective oxidation of alkynes (which can be prepared by Sonogashira coupl...

Claims

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Application Information

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IPC IPC(8): C07C45/28C07C49/784C07C49/84C07C49/813C07C49/788C07C303/40C07C311/16C07D263/22
CPCC07C45/28C07C303/40C07D263/22C07C49/784C07C49/84C07C49/813C07C49/788C07C311/16
Inventor 郭勋祥顾大伟
Owner SHANGHAI JIAO TONG UNIV
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