Synthetic method of 6-benzyl phenanthridine compounds

A technology of benzylphenanthridine and synthesis method, which is applied in the field of chemistry, can solve the problems of serious environmental pollution, dangerous raw material azide, harsh reaction conditions, etc., and achieve the effects of high reaction efficiency, easy post-processing, and mild reaction conditions

Active Publication Date: 2017-10-10
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (1) Grignard reagent method: high temperature and high pressure are required, and the reaction conditions are harsh; metal catalysis is required, and the synthesis cost is high; environmental pollution is large;
[0008] (2) Azidotrimethylsilane: The raw material azide used is very dangerous, and a large amount of acid needs to be added to the reaction system, causing serious environmental pollution
[0009] It can be seen that although there are multiple methods for preparing 6-benzylphenanthridines in the prior art, these methods have serious defects, which limit their application

Method used

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  • Synthetic method of 6-benzyl phenanthridine compounds
  • Synthetic method of 6-benzyl phenanthridine compounds
  • Synthetic method of 6-benzyl phenanthridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 6-benzylphenanthridine:

[0048]

[0049] At room temperature (25 °C), the reaction solvent toluene (2 mL) and a catalytic amount of organic base 1,4-diazabicyclo(2,2,2)octane (DABCO, 0.03 mmol, 0.1 equiv) were added to In the reaction tube, the reaction tube was continuously pumped-nitrogen 3 times, and then the oxidant di-tert-butyl hydroperoxide (DTBP, 0.75mmol, 2.5 equiv), the raw material toluene (2mL) and the raw material were continuously added to the reaction tube. 2-isocyanobiphenyl (0.3mmol, 1equiv), then stirred in an oil bath at a reaction temperature of 120°C for 24h, after the reaction was finished, the reaction solvent was directly spinned off, and column chromatography (300 mesh silica gel was filled in the column, The product was obtained after separation by using petroleum ether and ethyl acetate at a volume ratio of 40:1 as the eluent. The product was a yellow solid with a yield of 80%.

[0050] The data of the proton nuclear magnetic...

Embodiment 2

[0058] Synthesis of 6-(4-methylbenzyl)phenanthridine:

[0059]

[0060] At room temperature (25 °C), the reaction solvent p-xylene (2 mL) and a catalytic amount of the organic base 1,4-diazabicyclo(2,2,2)octane (DABCO, 0.03 mmol, 0.1 equiv) Join in the reaction tube, the reaction tube is continuously carried out 3 times pumping-nitrogen gas operation, then continue to add oxidant di-tert-butyl hydroperoxide (DTBP, 0.75mmol, 2.5equiv), raw material p-xylene ( 2mL) and raw material 2-isocyanobiphenyl (0.3mmol, 1equiv), then stirred in an oil bath at a reaction temperature of 120°C for 24h. 300 mesh silica gel, petroleum ether and ethyl acetate volume ratio 40:1 as the eluent) were separated to obtain the product, the product was a yellow solid, and the yield was 78%.

[0061] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0062] 1 H NMR (500MHz, CDCl 3 )δ8.58(1H,d),8.52(1H,d),8.18-8.20(m,2H),7.71-7.76(m,2H),7.61-7.64(m,1H),7...

Embodiment 3

[0069] Synthesis of 6-(3-methylbenzyl)phenanthridine:

[0070]

[0071] At room temperature (25 °C), the reaction solvent m-xylene (2 mL) and a catalytic amount of the organic base 1,4-diazabicyclo(2,2,2)octane (DABCO, 0.03 mmol, 0.1 equiv) Join in the reaction tube, the reaction tube is continuously carried out 3 times of pumping-nitrogen gas operation, then continue to add oxidant di-tert-butyl hydroperoxide (DTBP, 0.75mmol, 2.5equiv), raw material m-xylene ( 2mL) and raw material 2-isocyanobiphenyl (0.3mmol, 1equiv), then stirred in an oil bath at a reaction temperature of 120°C for 24h. 300 mesh silica gel, petroleum ether and ethyl acetate volume ratio 40:1 as the eluent) to obtain the product after separation, the product is a yellow solid, the yield is 73%.

[0072] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0073] 1 H NMR (500MHz, CDCl 3 )δ:8.59(d,1H),8.54(d,1H),8.18-8.22(m,2H),7.72-7.77(m,2H),7.62-7.66(m,1H),7...

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Abstract

The invention discloses a synthetic method of 6-benzyl phenanthridine compounds. A reaction equation is as follows: formula (shown in the description), wherein R represents hydrogen, fluorine, chlorine, methyl, methoxyl or a naphthalene ring. The synthetic method has the beneficial effects that (1) the operation of the preparation process is simple and convenient, and the post-treatment of obtained products is easy; (2) high temperature and high pressure conditions are not required, and reaction conditions are mild; (3) a catalyst is not required, and the synthetic cost is lowered; (4) functional groups of a reaction substrate are high in tolerance, and the substrate is wide in range and easy to prepare; (5) an oxidant is cheap, easily available and relatively economic; (6) the reaction is efficient and high in yield; and (7) the synthetic method is pollution-free and environment-friendly.

Description

technical field [0001] The invention relates to a method for synthesizing a class of organic compounds, in particular to a method for synthesizing 6-benzylphenanthridine compounds, and belongs to the technical field of chemistry. Background technique [0002] 6-benzylphenanthridine compounds are common structural units in a class of natural products. Many natural products containing phenanthridine structural units have shown good pharmacological activities, and the representatives are three balls of phenanthridine and chlorinated double-faced needles. Alkaline (has anti-liver cancer activity), Xanthanine alkali. Some benzophenanthridine compounds have anti-liver cancer, anti-nasopharyngeal cancer and anti-gastric cancer activities, and have a strong interaction with calf thymus DNA. It has been reported that benzophenanthridine compounds can be used as topoisomerase Ⅰ and topoisomerase Ⅱ inhibitors, thereby playing an anticancer role. [0003] It is precisely because 6-ben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 刘妙昌刘玮张鑫钱乐斌黄小波高文霞吴华悦
Owner WENZHOU UNIVERSITY
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