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Method for preparing benzylated quinoxalinone compound under visible light catalysis

A technology for benzylated quinoxalinone and quinoxalinone is applied in the field of preparation of benzylated quinoxalinone compounds, can solve the problems of reaction dependence, limited application, few synthesis methods, etc., and achieves mild conditions, Simple operation and high yield effect

Inactive Publication Date: 2021-11-23
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, benzylated quinoxalinones have significant biological activity and can be used as calcium channel blockers, aldose reductase inhibitors and antithrombotic drugs (Tetrahedron Lett., 2014, 55, 3299; ChemMedChem, 2013, 8,1913; Bioorganic & Medicinal Chemistry Letters,2003,13,2297), but there are few synthetic methods for benzylated quinoxalinones, and the reaction depends on transition metals and strong oxidants, which greatly limits its use in drug synthesis practical application of

Method used

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  • Method for preparing benzylated quinoxalinone compound under visible light catalysis
  • Method for preparing benzylated quinoxalinone compound under visible light catalysis
  • Method for preparing benzylated quinoxalinone compound under visible light catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In an 8mL reaction flask was added N-methyl-2(1H)quinoxalinone (0.1mmol), benzyl bromide (0.12mmol), sodium acetate (0.12mmol), xanthate (0.01mmol) in 2mL of 1, 2-dichloroethane was irradiated with blue light at 60 degrees Celsius and stirred for 12 hours. After the reaction was completed, the solvent was extracted, dried, and rotary evaporated to remove the solvent. The residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) , the yield of the final product was 90%.

[0022] The specific results are as follows:

[0023]

[0024] Yellow solid (22.5 mg, 90%); 1 H NMR (400MHz, Chloroform-d) δ 7.86 (dd, J=7.99, 1.38Hz, 1H), 7.56–7.44 (m, 3H), 7.38–7.24 (m, 4H), 7.26–7.21 (m, 1H) ), 4.27(s, 2H), 3.67(s, 3H); 13 C NMR (101 MHz, Chloroform-d) δ 159.3, 154.7, 137.1, 133.4, 132.8, 130.0, 129.9, 129.5, 128.4, 126.6, 123.6, 113.6, 40.8, 29.1.

Embodiment 2

[0026] In an 8 mL reaction flask was added N-ethyl acetate-2(1H)quinoxalinone (0.2 mmol), benzyl bromide (0.24 mmol), NaOAc (0.24 mmol), xanthate (0.02 mmol) in 4 mL of 1, 2-dichloroethane was irradiated with blue light at 60 degrees Celsius and stirred for 12 hours. After the reaction was completed, the solvent was extracted, dried, and rotary evaporated to remove the solvent. The residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) , the yield of the final product was 89%. The specific results are as follows:

[0027]

[0028] Yellow solid (57.2 mg, 89%); 1 H NMR (400MHz, Chloroform-d) δ 7.86 (d, J=7.90Hz, 1H), 7.46 (dd, J=14.08, 7.27Hz, 3H), 7.29 (m, 7.32-7.18Hz, 3H), 7.20 (t, J=7.28Hz, 1H), 7.02(d, J=8.30Hz, 1H), 4.97(s, 2H), 4.27(s, 2H), 4.21(q, J=7.11Hz, 2H), 1.23 (t, J=7.13Hz, 3H); 13 C NMR (101MHz, Chloroform-d) δ 167.1, 159.1, 154.3, 136.8, 132.8, 132.5, 130.3, 130.1, 129.5, 128.4, 126.6, 123.9, 113.0, 62.1, 43.6, 40.6,...

Embodiment 3

[0034] In an 8mL reaction flask was added N-allyl-2(1H)quinoxalinone (0.2mmol), benzyl bromide (0.24mmol), NaOAc (0.24mmol), xanthate (0.02mmol) in 4mL of 1, 2-dichloroethane was irradiated with blue light at 60 degrees Celsius and stirred for 12 hours. After the reaction was completed, the solvent was extracted, dried, and rotary evaporated to remove the solvent. The residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) , the yield of the final product was 88%. The specific results are as follows:

[0035]

[0036] Yellow solid (48.5 mg, 88%); 1 H NMR (400MHz, Chloroform-d) δ 7.85 (dd, J=8.00, 1.42 Hz, 1H), 7.46 (m, 3H), 7.29 (m, 3H), 7.25–7.18 (m, 2H), 5.89 ( m, 1H), 5.26–5.21 (m, 1H), 5.16–5.10 (m, 1H), 4.87–4.80 (m, 2H), 4.28 (s, 2H); 13C NMR (101 MHz, Chloroform-d) δ 159.4, 154.3, 137.1, 132.9, 132.6, 130.6, 130.0, 129.8, 129.5, 128.4, 126.6, 123.6, 118.1, 114.1, 44.6, 40.7.

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Abstract

The invention discloses a method for preparing a benzylated quinoxalinone compound under visible light catalysis. The benzylated quinoxalinone compound is synthesized under the irradiation of visible light by taking a quinoxalinone compound and benzyl bromide as raw materials, xanthate as a catalyst and sodium acetate (NaOAc) as an additive. The method has the advantages of mild reaction conditions, simplicity and convenience in operation, no oxidant, wide substrate application range and the like. The compound has potential application value in the research fields of medicine, organic synthesis and the like, can be used for synthesizing a drug molecule, namely an aldose reductase inhibitor and a structural molecule with anti-depression activity, and provides a new preparation method for synthesis of benzylquinoxalinone compounds.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and medicinal chemistry, in particular to a preparation method of benzylated quinoxalinone compounds. Background technique [0002] Quinoxalinones have unique physical, chemical and biological activities, and are widely used in anti-inflammatory, bactericidal, antithrombotic and antitumor applications. Among them, benzylated quinoxalinone has significant biological activity and can be used as calcium channel blocker, aldose reductase inhibitor and antithrombotic drug, etc. (Tetrahedron Lett., 2014, 55, 3299; ChemMedChem, 2013, 8, 1913; Bioorganic & Medicinal Chemistry Letters, 2003, 13, 2297), but currently there are few synthetic methods for benzylated quinoxalinone, and the reaction depends on transition metals and strong oxidants, which greatly limits its use in drug synthesis. practical application. Therefore, the development of simple, fast and efficient preparation methods for the synthe...

Claims

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Application Information

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IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 於兵孙凯相盼洁陈晓岚屈凌波
Owner ZHENGZHOU UNIV
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