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Method for preparing 2-phenylselenite sulfuryl quinoxaline compound through zinc catalysis

A technology for phenylselenosulfone-based quinoxaline and catalytic preparation, which is applied in the direction of organic chemistry and the like, and can solve the problems of difficult to handle by-products, many reaction steps, low reaction efficiency and the like

Inactive Publication Date: 2021-07-13
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The reported preparation method of 2-phenylselenoxide sulfone quinoxaline compounds is mainly through metal catalysis, and can be obtained through multi-step coupling and oxidation. There are many reaction steps, low reaction efficiency and a series of difficult to produce in the reaction process. Disadvantages such as by-products of processing

Method used

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  • Method for preparing 2-phenylselenite sulfuryl quinoxaline compound through zinc catalysis
  • Method for preparing 2-phenylselenite sulfuryl quinoxaline compound through zinc catalysis
  • Method for preparing 2-phenylselenite sulfuryl quinoxaline compound through zinc catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of product 4a

[0041] At room temperature, in a 50mL round bottom flask, add 10mmol quinoxaline, 12mmol sodium selenide and 10mmol iodobenzene, then add 30mL DMF, 1mmol zinc sulfate and 20mmol cesium carbonate successively, and stir at 70°C for 8 Hour. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain The pure product of 2-phenylselenoxide sulfonylquinoxaline compound 4a.

[0042] 4a 1 H NMR spectrum see figure 1 , 13 C NMR spectrum see figure 2 .

[0043] 2-(Phenylseleninyl)quinoxaline(4a)White solid, 122mg, 81% yield, m.p.157-159℃;

[0044] 1 H NMR (400MHz, CDCl 3 )δ9.53(s, 1H), 8.02(d, J=7.7Hz, 2H), 7.65(d, J=8.0Hz, 1H), 7.53(t, J=7.3Hz, 1H), 7.45(dd, J=18.0,8.4Hz,3H),7.32-7.28(m,1H),7.22(s,1H),7.15(t,J=7.1Hz,1H); 13 C NMR (101MHz, CDCl 3 )δ...

Embodiment 2

[0046] Embodiment 2: the preparation of product 4b

[0047]At room temperature, in a 50mL round bottom flask, add 10mmol quinoxaline, 12mmol sodium selenide and 10mmol iodine naphthalene, then add 30mL DMF, 1mmol zinc sulfate and 20mmol cesium carbonate successively, and stir at 70°C for 8 Hour. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain The pure product of 2-phenylselenoxide sulfonylquinoxaline compound 4b.

[0048] 4b 1 H NMR spectrum see image 3 , 13 C NMR spectrum see Figure 4 .

[0049] 2-(Naphthalen-2-ylseleninyl)quinoxaline(4b)White solid, 135mg, 77% yield, m.p.146-148℃;

[0050] 1 H NMR (400MHz, CDCl 3 )δ8.91(s,1H),8.61(s,1H),7.99-7.91(m,3H),7.87(d,J=7.7Hz,1H),7.68-7.58(m,3H),7.49-7.29 (m,3H),7.17(t,J=7.5Hz,1H); 13 C NMR (101MHz, CDCl 3 )δ 138.24, 137.07, 135.14, 13...

Embodiment 3

[0052] Embodiment 3: the preparation of product 4c

[0053] At room temperature, add 10mmol of 6-methylquinoxaline, 12mmol of sodium selenide and 10mmol of 4-methyliodobenzene in a 50mL round-bottomed flask, then add 30mL of DMF, 1mmol of zinc sulfate and 20mmol of carbonic acid Cesium, stirred at 70°C for 8 hours. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain The pure product of 2-phenylselenoxide sulfonylquinoxaline compound 4c.

[0054] 4c 1 H NMR spectrum see Figure 5 , 13 C NMR spectrum see Figure 6 .

[0055] 7-Methyl-2-(p-tolylseleninyl)quinoxaline(4c)White solid, 120mg, 73% yield, m.p.132-135℃;

[0056] 1 H NMR (400MHz, CDCl 3 )δ8.88(s,1H),7.87(d,J=8.4Hz,2H),7.42(s,1H),7.29(dd,J=8.3,5.3Hz,3H),7.15(dd,J=8.5 ,1.5Hz,1H),7.09-7.07(m,1H),2.41(s,3H),2.38(s,3H); 13 CNMR (101MH...

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Abstract

The invention discloses a method for preparing a 2-phenylselenite sulfuryl quinoxaline compound as shown in a formula (IV) under the catalysis of zinc, which comprises the following steps: fully reacting a quinoxaline compound as shown in a formula (I), sodium selenide as shown in a formula (II) and an iodobenzene compound as shown in a formula (III) in a DMF (Dimethyl Formamide) solvent by taking zinc sulfate as a catalyst and sodium ethoxide as alkali to obtain the 2-phenylselenite sulfuryl quinoxaline compound is prepared. The method provided by the invention has the advantages of low catalyst cost, meeting of green and environment-friendly requirements, few synthesis steps and simple post-treatment, and is suitable for large-scale production of pharmaceutical and chemical intermediates.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical and chemical intermediates, and in particular relates to a zinc-catalyzed method for preparing 2-phenylselenoxidesulfonylquinoxaline compounds. Background technique [0002] 2-phenylselenoxide sulfonylquinoxaline compounds have extremely important functions and are widely used in the manufacture of medicine and functional materials. At the same time, the 2-phenylselenoxidesulfonylquinoxaline compounds can improve human immunity and have a good inhibitory effect on the replication and metastasis of tumor cells. 2-Phenylselenoxide sulfonylquinoxaline compounds significantly regulate immune function, which may be an important mechanism for selenium to inhibit tumors. In addition, 2-phenylselenoxide sulfone quinoxaline compounds have obvious antioxidant effects, can inhibit peroxidation, scavenge free radicals, and repair cell membrane damage. The 2-phenylselenoxide sulfone qui...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 徐润生金浩孙姗姗周欣妍
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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