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A kind of method for synthesizing quinoxaline compounds by double protein catalyzed cascade reaction

A cascade reaction and compound technology, applied in the field of biocatalytic synthesis, can solve the problems of too many synthesis steps and insufficient environmental protection, and achieve the effects of simple process, reduced separation and purification steps, and good product selectivity.

Active Publication Date: 2021-01-01
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a green method for synthesizing quinoxaline compounds by double protein catalyzed cascade reaction, to solve the problem that the existing quinoxaline compound preparation method proposed in the above-mentioned background technology has many synthetic steps and is not environmentally friendly enough The problem

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  • A kind of method for synthesizing quinoxaline compounds by double protein catalyzed cascade reaction
  • A kind of method for synthesizing quinoxaline compounds by double protein catalyzed cascade reaction
  • A kind of method for synthesizing quinoxaline compounds by double protein catalyzed cascade reaction

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Embodiment 1

[0045] A method for synthesizing quinoxaline compounds through double protein catalyzed cascade reaction, the steps are as follows:

[0046] In 2ml of water, bovine hemoglobin (0.1mol%, i.e. 1 μmol) and porcine chymolipase (PPL, 20mg) were used as catalysts, and after adding 5%mol of TritonX-100 as a surfactant, 108.0mg of phthalate was added. Diamine, 139.2 mg of methyl acetoacetate and 197.2 mg of p-toluenesulfonyl azide were stirred and reacted at 55° C. for 6 h. The reaction progress was detected by thin-layer chromatography. After the reaction was completed, ethyl acetate was added for extraction, and then washed with hydrochloric acid, dried with anhydrous magnesium sulfate, and concentrated. Further purify with silica gel column chromatography (ethyl acetate / n-hexane) afterwards, obtain quinoxaline compound (methyl 3-methyl-2-quinoxaline carboxylate 183.82mg, white solid, productive rate 91% ).

[0047] Concrete reaction formula is as follows:

[0048]

[0049] Fu...

Embodiment 2

[0053] A method for synthesizing quinoxaline compounds through double protein catalyzed cascade reaction, the steps are as follows:

[0054] In 2ml of water, bovine hemoglobin (0.1mol%, i.e. 1 μmol) and porcine chymolipase (PPL, 20mg) were used as catalysts, and after adding 5%mol of TritonX-100 as a surfactant, 108.0mg of phthalate was added Diamine, 156.0 mg of ethyl acetoacetate and 197.2 mg of p-toluenesulfonyl azide were stirred and reacted at 55° C. for 6 h. The reaction progress was detected by thin-layer chromatography. After the reaction was completed, ethyl acetate was added for extraction, and then washed with hydrochloric acid, dried with anhydrous magnesium sulfate, and concentrated. Afterwards, it was further purified by silica gel column chromatography (ethyl acetate / n-hexane) to obtain quinoxaline compounds (ethyl 3-methyl-2-quinoxaline carboxylate 194.6 mg; yield 90%, white solid) .

[0055] Concrete reaction formula is as follows:

[0056]

[0057] Furt...

Embodiment 3

[0061] A method for synthesizing quinoxaline compounds through double protein catalyzed cascade reaction, the steps are as follows:

[0062] In 2ml of water, bovine hemoglobin (0.1mol%, i.e. 1 μmol) and porcine chymolipase (PPL, 20mg) were used as catalysts, and after adding 5%mol of TritonX-100 as a surfactant, 108.0mg of phthalate was added Diamine, 172.8mg of ethyl propionoacetate and 197.2mg of p-toluenesulfonyl azide were stirred and reacted at 55°C for 6h. The reaction progress was detected by thin-layer chromatography. After the reaction was completed, ethyl acetate was added for extraction, and then washed with hydrochloric acid, dried with anhydrous magnesium sulfate, and concentrated. Afterwards, it was further purified by silica gel column chromatography (ethyl acetate / n-hexane) to obtain quinoxaline compounds (ethyl 3-ethyl-2-quinoxaline carboxylate 202.6 mg; yield 88%, white solid) .

[0063] Concrete reaction formula is as follows:

[0064]

[0065] Further...

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Abstract

The invention relates to the technical field of biological catalytic synthesis and particularly discloses a method for synthesizing quinoxaline compounds by a double-protein catalytic cascade reaction. The method comprises the steps as follows: a beta-keto ester compound, substituted o-phenylenediamine and methylphenylsulfonyl azido are taken as reactants to be dissolved in a solvent, a catalyst and a surfactant are added, the mixture is stirred to react to produce a product, and the product is sequentially dried, concentrated and purified, wherein the solvent is water, and the catalyst is procine pancreaslipase (PPL) and hemoglobin from bovine blood (HbBv). The process is convenient, a heme protein catalytic carbene reaction and a lipase protein catalytic reaction are coupled to constructa green method for synthesizing quinoxaline compound by double proteins by a one-pot method, the target product can be rapidly and conveniently synthesized, meanwhile, synthesis is completed in water, and the problems that the existing quinoxaline compound preparation method comprises more synthesis steps and is not green and environmentally friendly enough are solved.

Description

technical field [0001] The invention relates to the technical field of biocatalytic synthesis, in particular to a method for synthesizing quinoxaline compounds through double protein catalytic cascade reaction. Background technique [0002] Quinoxaline is an important fine chemical intermediate, which is widely used in pesticide, pharmaceutical and other industries, and has certain importance and practicability. Among them, quinoxaline derivatives (quinoxaline compounds), as a class of important benzopyrazine heterocyclic compounds, have a wide range of biological activities (such as antitumor, antiviral, antibacterial, anti-inflammatory, anti-HIV, etc. activity), it can be used as a backbone molecule in pharmaceutical preparation. In addition, quinoxaline compounds can also be used as synthetic intermediates for products such as fuels, organic semiconductors, and solar cells. [0003] At present, there are many chemical methods to synthesize quinoxaline compounds. Among ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44
CPCC12P17/12
Inventor 王磊李正强李奉熙唐旭勇许雅宁王春宇王智
Owner JILIN UNIV
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