Preparation method of 6-phosphoryl substituted phenanthridine derivative

A technology of derivatives and phosphoryl groups, which is applied in the field of preparation of 6-phosphorylphenanthridine derivatives, can solve the problems of complex post-processing, waste of raw materials, harsh reaction conditions, etc., achieve scientific and reasonable synthesis methods, reduce production costs, The effect of simple synthesis method

Active Publication Date: 2017-04-26
蚌埠弘景科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Yet these preparation methods have obvious shortcoming: 1) raw material biphenyl isonitrile is difficult to prepare; 2) these methods all use excessive oxidizing agent, aftertreatment is complicated, and production cost is high; 3) reaction needs at least 2.5 times of equivalent Arylphosphine, waste a lot of raw materials, harsh reaction conditions, not in line with atom economy, lack of practical value

Method used

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  • Preparation method of 6-phosphoryl substituted phenanthridine derivative
  • Preparation method of 6-phosphoryl substituted phenanthridine derivative
  • Preparation method of 6-phosphoryl substituted phenanthridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of 6-phosphorylphenanthridine 3a

[0022]

[0023] To a 10ml thick-walled pressure-resistant tube, add biphenylisothiocyanate 1a (0.4mmol, 84.4mg), diarylphosphine 2a (0.6mmol, 121.2mg), manganese acetate tetrahydrate (0.4mmol, 98.1mg), N,N-dimethylformamide (2ml) was added, after the addition was complete, the reaction was carried out at 110°C for 6.0h. After the reaction system was cooled, 10 ml of ethyl acetate was added to dilute the reaction system, and washed with 30 ml of saturated sodium chloride solution six times, the organic phases were combined, dried by adding magnesium sulfate for 30 minutes, filtered, and the filtrate was concentrated by rotary evaporation to obtain a crude product. The crude product was separated by column (200-300 mesh silica gel) with eluent (petroleum ether: ethyl acetate=2:1), and the white solid product was confirmed to be 6-phosphorylphenanthridine 3a by NMR, and the yield was 68 %.

[0024] Spectrum analysis data ...

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other experimental conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 3b:

[0030] 1 H NMR (CDCl 3 ,500MHz):δ2.56(s,3H),7.42-7.45(m,4H),7.51(t,J=7.3Hz,2H),7.65-7.72(m,3H),7.94(q,J=6.3 Hz,4H),8.03(d,J=7.9Hz,1H),8.54(d,J=3.7Hz,2H),9.33(s,1H). 13 C NMR (CDCl 3 ,125MHz): δ21.9,121.9,124.4,127.7,128.1(d,J=12.0Hz),128.7,130.5,131.0,131.6,132.3(d,J=8.0Hz),132.8(d,J=16.4Hz), 133.6, 138.1, 142.4(d, J=23.9Hz), 156.3(d, J=128.7Hz).

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, and other experimental conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0033]

[0034] Spectral analysis data 3c:

[0035] 1 H NMR (CDCl 3 ,500MHz):δ3.94(s,3H),7.43-7.48(m,5H),7.64(t,J=7.4Hz,2H),7.69(t,J=7.6Hz,2H),7.97(q, J=6.3Hz, 4H), 8.04(d, J=8.1Hz, 1H), 8.50(d, J=7.9Hz, 1H), 8.54(d, J=9.1Hz, 1H), 9.03(d, J= 2.2Hz,1H). 13 C NMR (CDCl 3 ,125MHz):δ55.6,107.5,121.6,122.6,123.6,124.5,127.1,127.6,128.1(d,J=11.4Hz),128.8,129.4(d,J=22.9Hz),131.1,131.6,132.3(d, J=7.9Hz), 132.6, 133.5, 142.1(d, J=22.8Hz), 155.5(d, J=129.6Hz), 158.8.

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Abstract

The invention discloses a preparation method of a 6-phosphoryl substituted phenanthridine derivative, and belongs to the technical field of organic synthesis. The method comprises the steps that biphenyl isothiocyanate and diaryl oxygen and phosphorus are added into a reactor, by being catalyzed by manganese, heating is conducted in a solvent, after a reaction is completed, cooling is conducted to reach room temperature, a system is diluted with ethyl acetate and washed with saturated sodium chloride, an organic phase is combined, a filtrate is concentrated through a rotary evaporator, a coarse product is obtained, and finally a product is obtained through column chromatography separation. The synthetic method is easy to implement, raw materials are easy to prepare, multiple substituent groups are introduced simultaneously, the product is easy to purify and separate, the yield is high, and the method is suitable for synthesizing the 6-phosphoryl substituted phenanthridine derivative. The reaction equation of the derivative is defined in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of 6-phosphorylphenanthridine derivatives. Background technique [0002] As an important class of organic compounds, phosphorus-containing organic molecules are widely used in various fields such as organic synthetic chemistry, medicinal chemistry, and material chemistry. At the same time, organophosphorus, as an important class of ligands, also plays a vital role in metal-catalyzed organic synthesis and coordination chemistry. [0003] Phenanthridine is not only the core structural unit of many natural products, but also the basic skeleton of many important drug molecules. Many molecules containing phenanthridine skeletons have shown anticancer and antibacterial biological activities. The introduction of phosphorus atoms into the phenanthridine framework has potential application value. [0004] In recent years, the synthesis method of 6-phospho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/576
CPCC07F9/5765
Inventor 文丽荣窦谦郭维斯李明
Owner 蚌埠弘景科技有限公司
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