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A kind of 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: 2017-10-20
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A kind of preparation method of quinoxaline compounds
  • A kind of preparation method of quinoxaline compounds
  • A kind of preparation method of quinoxaline compounds

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Experimental program
Comparison scheme
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 to obtain 212 mg (98%) of pure compound 3-1.

[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] Compound 3-2 was prepared in the same manner as Compound 3-1, except that α-TEMPO-substituted methyl acetoacetate was used instead of α-TEMPO-substituted ethyl acetoacetate.

[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 technical field of synthesis of quinoxaline derivatives. The main points of the technical scheme of the present invention are: a preparation method of quinoxaline compounds, which comprises the following steps: o-phenylenediamine compound 1 and α-position 2,2,6,6-tetramethylpiperidine oxide substituted 1,3 -Dicarbonyl compound 2 prepares quinoxaline compound 3 by series reaction in acidic solvent. The present invention is a series of synthesis of o-phenylenediamine compounds and 1,3-dicarbonyl compounds substituted with α-position 2,2,6,6-tetramethylpiperidine oxide to construct quinoxaline structure skeleton through domino reaction Quinoxaline derivatives, the synthesis process is simple and easy to control, and the structure of target products is diverse, which lays the foundation for the synthesis of drug molecules containing 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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Patent Type & Authority Patents(China)
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