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Supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4h-pyran compounds

A technology of imidazole ionic liquid and ionic liquid, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve by-product environmental pollution, low atom utilization, Problems such as high production cost, to achieve the effect of increasing product yield, promoting the positive movement of reaction balance, and easy operation

Active Publication Date: 2022-03-18
CHINA THREE GORGES UNIV
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  • Description
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Problems solved by technology

At present, due to the lack of effective catalysts, the reported preparation methods (Vishnupriya R, Suresh J, Sivakumar S, et al. 4-(4-Fluorophenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3 -carbonitrile[J].2013,69(Pt 3):o451-o451.) There are more or less low utilization rate of atoms, low yield, serious waste of raw materials in short supply, high production cost, and serious damage to the environment caused by by-products Pollution and other issues have prompted scientists at home and abroad to work hard to explore new synthetic methods and routes
Among them, 2-amino-3-cyano-4H-pyran was synthesized in water (Shi, D.Q., Zhang, S., Zhuang, Q.Y., Tu, S.J., & Hu, H.W..(2003). Clean synthesis of 2-amino -3-cyano-4-aryl-7,7-dimethyl-5-oxo-4h-5,6,7,8-tetrahydrobenzo[b]pyran inwater.Chinese Journal of Organic Chemistry,23(8),877-879 .) It has the advantages of cleaning and environmental protection, but the operation is more cumbersome

Method used

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  • Supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4h-pyran compounds
  • Supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4h-pyran compounds
  • Supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4h-pyran compounds

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preparation example Construction

[0038] The preparation method of the KIT-6 loaded imidazolium ionic liquid of embodiment, comprises the following steps:

[0039] (1) N-methylimidazole, sodium ethoxide and ethanol solvent were reacted at 60-100°C for 7-10 hours, the solvent was recovered, and the product was dried to obtain intermediate 1;

[0040] (2) Intermediate 1, 3-chloropropyltriethoxysilane and acetonitrile solvent were reacted at 60-100°C for 10-20 hours, the solvent was recovered, and the product was dried to obtain Intermediate 2;

[0041] (3) Intermediate 2, n-bromobutane and toluene solvent were reacted at 80-120°C for 24-48 hours, the solvent was recovered, and the product was dried to obtain Intermediate 3;

[0042] (4) Intermediate 3, ionic liquid raw material and methanol solvent are reacted at 50-60° C. for 12-24 hours, the solvent is recovered, and the product is dried to obtain an ionic liquid;

[0043] (5) React ionic liquid 4, KIT-6 and ethanol solvent at 60-100° C. for 12-24 hours, reco...

Embodiment 1

[0047] In the reaction flask, add benzaldehyde (10mmol), malononitrile (10mmol), ethyl acetoacetate (10mmol), KIT-6 supported vanadate imidazole ionic liquid catalyst (0.5g), ethanol (20mL), oil bath Heating and stirring, the temperature is controlled at 80 ° C, and the stirring is continued for 3 hours after the temperature is stable. After the reaction is completed, the filtrate is recovered by filtration, the filter cake is washed, recrystallized, and dried to obtain 2-amino-3-cyano-4H-pyran. The yield is 51.4%.

Embodiment 2

[0049] In the reaction flask, add benzaldehyde (10mmol), malononitrile (10mmol), ethyl acetoacetate (10mmol), KIT-6 supported ethoxylate imidazole ionic liquid catalyst (0.5g), ethanol (20mL), oil bath Heat and stir, control the temperature at 50°C, continue stirring for 3 hours after the temperature is stable, filter and recover the filtrate after the reaction is completed, wash the filter cake, recrystallize and dry to obtain 2-amino-3-cyano-4H-pyran, the yield is 50.3%.

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Abstract

The invention discloses a method for catalytically synthesizing 2-amino-3-cyano-4H-pyran compounds with a loaded imidazole ionic liquid. The method uses malononitrile, aryl aldehyde and ethyl acetoacetate as raw materials, and under the catalysis of KIT-6 loaded imidazole ionic liquid, condensation and Michael addition reaction occur to synthesize 2-amino-3-cyano-4H ‑Pyrans. The invention has the advantages of simple operation, mild reaction conditions, less catalyst consumption and high catalytic efficiency, is clean and environment-friendly, and is a green and environment-friendly preparation method.

Description

technical field [0001] The invention relates to a method for catalytically synthesizing 2-amino-3-cyano-4H-pyran compounds with a KIT-6 loaded imidazole ionic liquid, belonging to the technical field of fine chemicals. [0002] technical background [0003] 4H-pyran is an important synthetic intermediate for the construction of heterocyclic compounds, and its derivatives have various biological and pharmacological activities. There have been reports on anti-allergic, anti-aging, anti-cytotoxic activity and inhibition of cancer cells. For example: Wang J L et al. found that compound HA14-1 has the effect of inhibiting cancer cells; Pyran derivatives can be used as inhibitors of non-peptide HIV (HIV-1) protease; the new Spiro Pyrano[23-d]thiazole derivatives synthesized by Zeinab A et al. have certain photochemical properties and anti-inflammatory and antibacterial properties . [0004] 2-Amino-3-cyano-4H-pyran is used in the synthesis of pyropyridine derivatives with potenti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07D311/74
CPCB01J31/0295B01J31/0284C07D311/74
Inventor 胡玉林李精锐陈卫丰刘湘
Owner CHINA THREE GORGES UNIV
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