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A kind of synthetic method of quinoxaline-2(1h)-ketone C-3 phosphonic acid compound

A synthesis method and quinoxaline technology are applied in the field of synthesis of quinoxaline-2-one C-3 phosphonic acid compounds, and can solve the problems of harsh reaction conditions, complicated reaction steps, narrow substrate range and the like. Easy to handle, green post-processing, wide range of substrates

Active Publication Date: 2017-06-20
HUAQIAO UNIVERSITY
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  • Claims
  • Application Information

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Problems solved by technology

In recent years, organophosphorus chemistry has developed rapidly, and phosphorus-containing heterocyclic compounds have great application space. However, some traditional synthetic methods often have complex reaction steps, harsh reaction conditions, long reaction time, many by-products, low yields, and low yields. The range of substances is narrow, and strong oxidants and other non-green and environmentally friendly reagents are required.

Method used

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  • A kind of synthetic method of quinoxaline-2(1h)-ketone C-3 phosphonic acid compound
  • A kind of synthetic method of quinoxaline-2(1h)-ketone C-3 phosphonic acid compound
  • A kind of synthetic method of quinoxaline-2(1h)-ketone C-3 phosphonic acid compound

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Experimental program
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Embodiment 1

[0022] Preparation of Dimethyl(3-oxo-3,4-dihydroquinoxalin-2yl)phosphonate

[0023] Put 0.2mmol of quinoxalin-2(1H)-one, 0.6mmol of dimethyl phosphate, 0.6mmol of potassium persulfate, and 2.0mL of acetonitrile into a 10mL reaction tube, place in an oil bath at 100°C, and Under the reaction 8h. Stop the reaction and cool to room temperature. The reaction solution was spin-dried with a rotary evaporator, and separated by column chromatography to obtain 46.7 mg of the target product with a yield of 92%. The compound is characterized as follows: 1 H NMR (400MHz, d 6 -DMSO) δ12.79(s, 1H), 7.89(d, J=8.0Hz, 1H), 7.69-7.63(m, 1H), 7.40-7.33(m, 2H), 3.87(d, J=11.1Hz , 6H). 13 C NMR (100MHz, d 6 -DMSO) δ154.5 (d, J C-P =31.4Hz), 153.8(d, J C-P =223.8Hz), 133.5(s), 133.2(d, J C-P =2.9Hz), 132.0(d, J C-P =25.3Hz), 130.3(s), 124.3(s), 116.3(s), 54.5(d, J C-P =6.3Hz). 31 P NMR (162MHz, d 6 -DMSO)δ9.4(s).HRMS m / z(ESI)calculated for C 10 h 11 N 2 o 4 P(M+H) + 255.0535, foun...

Embodiment 2

[0025] Preparation of Diethyl(3-oxo-3,4-dihydroquinoxalin-2yl)phosphonate

[0026] Put 0.2mmol of quinoxalin-2(1H)-one, 0.6mmol of diethyl phosphate, 0.6mmol of potassium persulfate, and 2.0mL of acetonitrile into a 10mL reaction tube, place in an oil bath at 100°C, and Under the reaction 8h. Stop the reaction and cool to room temperature. The reaction solution was spin-dried with a rotary evaporator, and separated by column chromatography to obtain 47.9 mg of the target product with a yield of 85%. The compound is characterized as follows: 1 H NMR (400MHz, d6-DMSO) δ 12.78 (s, 1H), 7.88 (d, J = 7.9Hz, 1H), 7.70-7.63 (m, 1H), 7.42-7.31 (m, 2H), 4.26 ( dq, J1=14.2Hz, J2=7.1Hz, 4H), 1.32(t, J=7.0Hz, 6H). 13 C NMR (100MHz, d6-DMSO) δ154.4(d, JC-P=31.4Hz), 154.2(d, JC-P=222.9Hz), 133.4(s), 133.2(d, JC-P=2.6Hz ), 131.9(d, JC-P=25.2Hz), 130.3(s), 124.3(s), 116.3(s), 63.8(d, JC-P=6.2Hz), 16.8(d, JC-P=6.1 Hz). 31 P NMR (162MHz, d6-DMSO) δ7.0(s). HRMS m / z (ESI) calculated for C1...

Embodiment 3

[0028] Preparation of Diisopropyl(3-oxo-3,4-dihydroquinoxalin-2yl)phosphonate

[0029] Add 0.2mmol of quinoxalin-2(1H)-one, 0.6mmol of diisopropyl phosphate, 0.6mmol of potassium persulfate, and 2.0mL of acetonitrile into a 10mL reaction tube, place in an oil bath at 100°C, and air Under the condition of reaction 8h. Stop the reaction and cool to room temperature. The reaction solution was spin-dried with a rotary evaporator, and separated by column chromatography to obtain 41.8 mg of the target product with a yield of 67%. The compound is characterized as follows: 1 H NMR (400MHz, d 6 -DMSO) δ12.74 (s, 1H), 7.85 (d, J=7.9Hz, 1H), 7.69-7.63 (m, 1H), 7.37 (dd, J 1 =14.1,J 2 =7.4Hz, 2H), 4.82(dq, J 1 =12.4,J 2 =6.2Hz, 2H), 1.35(dd, J=6.0Hz, J 2 =4.7Hz, 12H). 13 C NMR (100MHz, d 6 -DMSO) δ154.6 (d, J C-P =223.5Hz), 154.3(d, J C-P = 31.4Hz), 133.2(s), 133.1(d, J C-P =2.6Hz), 130.2(s), 124.3(s), 116.2(s), 72.23(d, J C-P =6.2Hz), 24.57(d, J C-P =3.2Hz), 23.91(d, J C-...

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Abstract

The invention discloses a synthetic method for a 2(1H)-quinoxalinone C-3 site phosphate compound. The synthetic method includes the following steps: (1) dissolving 2(1H)-quinoxalinone derivatives, a phosphatized reagent and potassium persulfate in an organic solvent, and reacting for 7.7-8.3 h at the temperature of 99-102 DEG C in the air conditions; (2) cooling the reaction product obtained in the step (1) to room temperature, and performing separation and purification, so as to obtain the 2(1H)-quinoxalinone C-3 site phosphate compound. According to the synthetic method, raw materials are easy to obtain, the reaction condition is gentle, the addition of an additive, namely a metal catalyst is not needed, and the yield is high (up to 92%); besides, the range of substrates is wide, the reaction specificity is high, and aftertreatment is simple, convenient and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of a quinoxaline-2(1H)-one C-3 phosphonic acid compound. Background technique [0002] The quinoxaline-2(1H)-one compound is a common pharmacophore in the field of drug design. The derivatives of the core structure have a variety of pharmacological activities and are widely used as anti-tumor agents, anti-cancer agents, aldose reductase Inhibitors, antibacterial agents, etc., are a class of potential multi-purpose lead compounds, which have been used in different clinical trials and have broad development and application prospects. In recent years, organophosphorus chemistry has developed rapidly, and phosphorus-containing heterocyclic compounds have great application space. However, some traditional synthetic methods often have complex reaction steps, harsh reaction conditions, long reaction time, many by-products, low yields, and low yie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6509
Inventor 崔秀灵高铭李毅
Owner HUAQIAO UNIVERSITY
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