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Preparation method of quinoxaline compounds

A compound, the technology of quinoxaline, which is applied in the field of preparation of quinoxaline compounds, can solve the problems such as the limitation of synthetic molecular structure diversity, and achieve the effect of diverse structure of target products, simple and easy synthesis process

Active Publication Date: 2015-11-04
XINXIANG MEDICAL UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

The traditional synthesis method is mainly the condensation cyclization of o-phenylenediamine and 1,2-dicarbonyl compound. The diversity of synthetic molecular structure is limited by the reaction substrate. This patent designs a new construction of quinoxaline ring method, and synthesized a series of quinoxaline compounds with structural diversity, which laid the foundation for the further preparation of quinoxaline drugs

Method used

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  • Preparation method of quinoxaline compounds
  • Preparation method of quinoxaline compounds
  • Preparation method of quinoxaline compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Dissolve 1.0 mmol of 1,3-dicarbonyl compound and 1.0 mmol of 2,2,6,6-tetramethylpiperidine oxide in 20 mL of ethyl acetate, add 0.2 mmol of cerium ammonium nitrate and heat to 60 °C and stir for 30 Minutes, after the reaction is complete, filter to remove insoluble inorganic salts, remove ethyl acetate by rotary evaporation, and separate by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1) to obtain α-position 2,2,6,6-tetramethyl 1,3-dicarbonyl compounds substituted by base piperidine oxides, the 1,3-dicarbonyl compounds substituted by α-position 2,2,6,6-tetramethylpiperidinium oxides are used for quinoxaline compounds synthesis.

Embodiment 2

[0020]

[0021] Dissolve 108 mg (1.0 mmol) of the raw material compound o-phenylenediamine and 314 mg (1.1 mmol) of ethyl acetoacetate substituted by α-position TEMPO in 5.0 mL of glacial acetic acid, stir the reaction system at room temperature for 10 minutes, evaporate the acetic acid, add The residue was dissolved in ethyl acetate, washed twice with saturated sodium bicarbonate solution (30mL×2), the organic layer was separated, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation, column chromatography (eluent: petroleum ether: acetic acid Ethyl ester=5:1) isolated compound 3-1 Pure product 212mg (98%).

[0022] 1 H NMR (400 MHz, CDCl 3 ) δ 8.19 (dd, J = 8.3, 1.2 Hz, 1H), 8.05 (d, J = 8.3 Hz, 1H), 7.83 (ddt, J = 8.7, 7.0, 1.7 Hz, 1H), 7.77 (ddd, J = 8.7, 3.3, 1.7 Hz, 1H), 4.57 (qd, J = 7.1, 1.4 Hz, 2H), 2.96 (d, J = 1.5 Hz, 3H), 1.50 (td, J = 7.1, 1.5 Hz, 3H).

Embodiment 3

[0024]

[0025] In addition to using α-position TEMPO-substituted methyl acetoacetate instead of α-position TEMPO-substituted ethyl acetoacetate, in order to prepare the compound 3-1 Compounds are prepared in the same way 3-2 .

[0026] 1 H NMR (400 MHz, CDCl 3 ) δ 8.19 (dd, J = 8.4, 1.1 Hz, 1H), 8.05 (dd, J = 8.4, 1.0 Hz, 1H), 7.87-7.81 (m, 1H), 7.80-7.73 (m, 1H), 4.09 (s, 3H), 2.98 (s, 3H).

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Abstract

The invention discloses a preparation method of quinoxaline compounds, and belongs to the quinoxaline derivative synthesis technical field. The key point of the technical scheme comprises that the preparation method of the quinoxaline compounds comprises that an o-phenylendiamine compound 1 and an alpha-sited 2,2,6,6-tetramethylpiperidine-1-oxyl substituted 1,3-dicarbonyl compound 2 are subjected to a cascade reaction in an acidic solvent to obtain the quinoxaline compounds 3. The o-phenylendiamine compound and the alpha-sited 2,2,6,6-tetramethylpiperidine-1-oxyl substituted 1,3-dicarbonyl compound are subjected to domino reaction to construct a quinoxaline structural skeleton so as to synthesize a series of quinoxaline derivatives, the synthetic process is simple and easy to control, the structures of the target products are diverse, and a foundation is laid for synthesis of drug molecules containing the quinoxaline structures.

Description

technical field [0001] The invention belongs to the technical field of synthesis of quinoxaline derivatives, and in particular relates to a preparation method of quinoxaline compounds. Background technique [0002] The quinoxaline structure skeleton widely exists in the molecular structure of active natural products, medicines and pesticides. Compounds containing the quinoxaline core have multiple biological activities such as anticancer, antiviral, antibacterial, antiinfective and kinase inhibitory. In addition, quinoxalines are also used as dyes, luminescent materials, semiconductor materials, insecticides, and DNA cutting agents. Due to the wide range and important application value of quinoxaline, its synthesis has been paid close attention to. The traditional synthesis method is mainly the condensation cyclization of o-phenylenediamine and 1,2-dicarbonyl compound. The diversity of synthetic molecular structure is limited by the reaction substrate. This patent designs ...

Claims

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Application Information

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IPC IPC(8): C07D241/44C07D241/42
CPCC07D241/42C07D241/44
Inventor 闫建伟倪天军庄芳芳闫福林曹轲
Owner XINXIANG MEDICAL UNIV
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