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Preparation method of phenanthridine heterocyclic compounds

The technology of a compound, phenanthridine, is applied in the field of preparation of phenanthridine heterocyclic compounds, which can solve the problems of unfriendly bromide, poor functional group tolerance, environmental protection and greenness, etc., and achieve easy control and applicable scope of substrates Wide, important commercial value and the effect of industrial application prospects

Active Publication Date: 2018-07-20
NANJING AGRICULTURAL UNIVERSITY
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AI Technical Summary

Problems solved by technology

Although some synthetic methods can be used for the synthesis of phenanthridine compounds, there are not many preparation methods for phenanthridine derivatives substituted by the 6-position alkyl, and these methods have all used very expensive and toxic transition metal iridium catalysts. The substrate range of this method is very narrow, and the tolerance of functional groups is not good. It is limited to certain bromine-containing alkylation reagents, and bromines are often unfriendly to the environment and do not meet the requirements of environmental protection and greenness. Some methods also need to use more expensive Hypervalent iodine reagent with explosion hazard (Angew.Chem.Int.Ed.2013,52,13289; Angew.Chem.Int.Ed.2014,53,14451)

Method used

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  • Preparation method of phenanthridine heterocyclic compounds
  • Preparation method of phenanthridine heterocyclic compounds
  • Preparation method of phenanthridine heterocyclic compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2a (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL), and placed under a 18W white light for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation on a water pump under reduced pressure to obtain a crude product, which was passed through a chromatographic silica gel column. Purification (ethyl acetate:petroleum ether=1:40) gave 48.1 mg of yellow solid product 3aa with a yield of 83%.

[0035] Data representation: 1 H NMR (400MHz, CDCl 3 )δ8.61(d, J=8.4Hz, 1H), 8.53(d, J=8.0Hz, 1H), 8.21(d, J=8.0Hz, 1H), 8.10(d, J=8.0Hz, 1H) ,7.83(t,J=7.6Hz,1H),7.70(q,J=8.1Hz,2H),7.61(t,J=7.5Hz,1H),3.04(s,3H); 13 C NMR (100MHz, ...

Embodiment 2

[0037] Isocyanide 1a (0.30mmol), N-(acyloxy)phthalimide 2b (0.60mmol), eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL), and placed under a 18W white light for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation on a water pump under reduced pressure to obtain a crude product, which was passed through a chromatographic silica gel column. (Ethyl acetate:petroleum ether=1:40) purified to obtain 53.5 mg of white solid product 3ab, with a yield of 86%.

[0038] Data representation: 1 H NMR (400MHz, CDCl 3)δ8.62(d, J=8.3Hz, 1H), 8.52(d, J=8.2Hz, 1H), 8.25(d, J=8.2Hz, 1H), 8.14(d, J=8.1Hz, 1H) ,7.81(t,J=7.6Hz,1H),7.69(dt,J=8.0,7.2Hz,2H),7.61(t,J=7.5Hz,1H),3.41(q,J=7.6Hz,2H) ,1.51(...

Embodiment 3

[0040] Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2c (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL), and placed under a 18W white light for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation on a water pump under reduced pressure to obtain a crude product, which was passed through a chromatographic silica gel column. Purification (ethyl acetate:petroleum ether=1:40) gave 98.2 mg of white solid product 3ac with a yield of 86%.

[0041] Data representation: 1 H NMR (400MHz, CDCl 3 )δ8.61(d, J=8.0Hz, 1H), 8.51(d, J=8.0Hz, 1H), 8.23(d, J=8.0Hz, 1H), 8.14(d, J=8.0Hz, 1H) ,7.80(t,J=7.6Hz,1H),7.69(dt,J=15.2,7.4Hz,2H), 7.60(t,J=7.5Hz,1H),3.44–3.30(m,2H),1.92( dt...

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Abstract

The invention discloses a preparation method of phenanthridine heterocyclic compounds. With isonitrile and N-(acyloxy)phthalimide as raw materials, under the action of an organic small molecular catalyst, a reductive quenching agent and an alkali are added, a reaction is performed for 20-24 h under irradiation of white light, and thus the phenanthridine heterocyclic compounds are prepared. The preparation method is a visible light induced photochemical reaction, gets rid of harsh requirements of a traditional ultraviolet photochemical reaction on equipment, and can be effectively realized by using cheap household fluorescent lamps, LED lamps and inexhaustible clean energy sources (sun light). In addition, the visible light induced photochemical reaction usually has the advantages of mild reaction conditions, easy control, high efficiency and high yield of products. Therefore, the preparation method attracts extensive attention of synthesis chemists in recent years, and is developed into the key point and hot point of current researches.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a preparation method of phenanthridine heterocyclic compounds. Background technique [0002] Nitrogen-containing heterocyclic skeleton structures (such as phenanthridine, indole, quinoline and isoquinoline, etc.) widely exist in natural products, bioactive molecules, materials, pesticides and pharmaceutical molecules. Among them, phenanthridine compounds are a class of important compounds in the fields of organic chemistry and medicinal chemistry, and they have many biological and pharmaceutical activities, such as antitumor, antileukemia, antiviral and antifungal activities. NK109 is a kind of alkaloid containing phenanthridine structure, which has significant anti-tumor activity in medicine (Bioorg.Med.Chem.Lett.2000,10,2321), lycobetaine (lycobetaine) can be used It is suitable for the treatment of digestive tract cancer, liver cancer, ovarian cancer, lung cancer, head and nec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07D401/04C07D405/04
CPCC07D221/12C07D401/04C07D405/04
Inventor 朱映光曹淑君郭康彭琛石云
Owner NANJING AGRICULTURAL UNIVERSITY
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