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Ruthenium catalytic 3-substituted isocoumarin synthesis method

A technology of isocoumarin and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high cost, complicated process, low practicability, etc., and achieve the effect of less reaction steps and simple operation

Active Publication Date: 2019-10-22
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Description
  • Claims
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AI Technical Summary

Benefits of technology

This patented process involves activating certain chemicals called anisobors or naproxenic acids with strong coordination between two molecules like nitric oxide (NO) gas. These processes can help create various types of substances such as caffeoylene-3 -one-2'-methanol), flavonols, coumalate esters, etc., which have potential applications for use in medicine and biological researches.

Problems solved by technology

This patents discuss various techniques used by chemiststo make certain types of chemical called isocyclene that could potentially improve medical treatments or prevent diseases caused by bacteria or other microorganisms. These new methodologies involve isolating specific type of organobalt complexes containing three atoms of carbon attached together through a ring system consisting of two rings - one atom being connected to another atom at each end.

Method used

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  • Ruthenium catalytic 3-substituted isocoumarin synthesis method
  • Ruthenium catalytic 3-substituted isocoumarin synthesis method
  • Ruthenium catalytic 3-substituted isocoumarin synthesis method

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Embodiment 1

[0053]

[0054]The reactor was placed under nitrogen, and 0.40mmol (78.4mg) α-carbonylsulfide ylide (1a), 0.02mmol (12.2mg) [Ru(p-cymene)Cl 2 ] 2 , 0.08mmol (27.5mg) AgSbF 6 , 0.40mmol (24.0mg) AcOH, 2mL TFE, stirred at 100°C for 12h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography with a mixed solvent of petroleum ether and ethyl acetate as the eluent to obtain 40.5 mg of 3-substituted isocoumarin 2a with an isolated yield of 91%.

[0055] join figure 1 , figure 2 , the characterization data of compound 2a are as follows:

[0056] 1 H NMR (400MHz, CDCl 3 )δ8.29(d, J=8.4Hz, 1H), 7.87(dd, J=8.0, 1.6Hz, 2H), 7.72-7.68(m, 1H), 7.50-7.40(m, 5H), 6.94(s ,1H). 13 C NMR (100MHz, CDCl 3 ) δ 162.3, 153.6, 137.5, 134.9, 132.0, 130.0, 129.6, 128.8, 128.2, 126.0, 125.2, 120.5, 101.8.

Embodiment 2

[0058]

[0059] The reactor was placed under nitrogen, and 0.40mmol (84.0mg) α-carbonylsulfide ylide (1b), 0.02mmol (12.2mg) [Ru(p-cymene)Cl 2 ] 2 , 0.08mmol (27.5mg) AgSbF 6 , 0.40mmol (24.0mg) AcOH, 2mL TFE, stirred at 100°C for 12h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography with a mixed solvent of petroleum ether and ethyl acetate as the eluent to obtain 45.0 mg of 3-substituted isocoumarin 2b with an isolation yield of 90%.

[0060] join image 3 , Figure 4 , the characterization data of compound 2b are as follows:

[0061] 1 H NMR (400MHz, CDCl3) δ8.17 (d, J = 8.0Hz, 1H), 7.76 (d, J = 8.4Hz, 2H), 7.29-7.24 (m, 4H), 6.83 (s, 1H), 2.47 (s,3H),2.40(s,3H). 13 C NMR (100MHz, CDCl3) δ 162.5, 153.9, 145.9, 140.2, 137.8, 129.6, 129.5, 129.4, 129.3, 125.8, 125.1, 118.0, 101.1, 22.0, 21.4.

Embodiment 3

[0063]

[0064] The reactor was placed under nitrogen, and 0.40mmol (92.0mg) α-carbonylsulfide ylide (1c), 0.02mmol (12.2mg) [Ru(p-cymene)Cl 2 ] 2 , 0.08mmol (27.5mg) AgSbF 6 , 0.40mmol (24.0mg) AcOH, 2mL TFE, stirred at 100°C for 12h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography with a mixed solvent of petroleum ether and ethyl acetate as the eluent to obtain 48.9 mg of 3-substituted isocoumarin 2c with an isolation yield of 84%.

[0065] see Figure 5 , Figure 6 , the characterization data of compound 2c are as follows:

[0066] 1 H NMR (400MHz, CDCl3) δ8.23(d, J=8.4Hz, 1H), 7.81(d, J=8.4Hz, 2H), 7.49-7.44(m, 4H), 6.86(s, 1H). 13 C NMR (100MHz, CDCl3) δ 161.2, 153.8, 141.7, 138.7, 136.5, 131.4, 130.0, 129.2, 128.9, 126.6, 125.5, 118.8, 101.0.

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Abstract

The invention discloses a ruthenium catalytic 3-substituted isocoumarin synthesis method, wherein ruthenium is used as a catalyst, the ortho C-H bond activation of an aromatic hydrocarbon and an intramolecular ring closing reaction are achieved under weak coordination oxygen atom guiding action, and a variety of 3-substituted isocoumarin compounds are efficiently synthesized in one step through simple operation. According to the present invention, the synthesis method has characteristics of cheap and easily available reactant raw materials, fewer reaction steps, simple operation, step economyand market economy.

Description

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Claims

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Application Information

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Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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