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A kind of green catalytic method for preparing 2-amino-4h-chromene derivatives

A technology for catalytic preparation and derivatives, applied in organic chemistry and other directions, can solve the problems that ionic liquids are not easy to biodegrade, use a large amount of ionic liquids, and have high preparation costs, and achieve easy industrialized large-scale production, less catalyst use, and preparation process. simple effect

Inactive Publication Date: 2015-12-02
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the existence of ionic liquids in the process of preparing 2-amino-4H-chromene derivatives by alkaline ionic liquids in the prior art, which are not easy to biodegrade, the preparation price is high, the amount of ionic liquids used is large and they are being recycled. The amount of loss is also large and other disadvantages, and a kind of easy biodegradation, high alkalinity, simple preparation and low price Bronster alkaline ionic liquid is provided as a green catalyst, and water is used as a solvent to catalyze the preparation of 2-amino-4H -methods of chromene derivatives

Method used

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  • A kind of green catalytic method for preparing 2-amino-4h-chromene derivatives
  • A kind of green catalytic method for preparing 2-amino-4h-chromene derivatives
  • A kind of green catalytic method for preparing 2-amino-4h-chromene derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1: 10mmol benzaldehyde, 10mmol malononitrile, 10mmol resorcinol and 0.4mmol Bronster basic ionic liquid were added respectively to a 50ml single-necked bottle containing 4ml water with a stirring bar and a condenser tube. Under vigorous stirring, reflux reaction for 20 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, filtered with suction, the obtained filter residue was washed with water, dried and then recrystallized with methanol, vacuum After drying, pure 2-amino-7-hydroxy-3-cyano-4-phenyl-4H-chromene was obtained in 91% yield. Add benzaldehyde, malononitrile and resorcinol directly to the filtrate and reuse it.

[0024] 2-amino-7-hydroxy-3-cyano-4-phenyl-4H-chromene: m.p.231~232℃; 1 HNMR (300MHz, acetone-d 6 ): δ=4.73(s, 1H, CH), 5.65(s, 2H, NH 2 ), 6.62(d, J=3.0Hz, 1H, ArH), 6.69(dd, J=8.5, 3.0Hz, 1H, ArH), 6.96(d, J...

Embodiment 2

[0025] Embodiment 2: 10mmol p-methoxybenzaldehyde, 10mmol malononitrile, 10mmol resorcinol and 0.5mmol Bronster alkaline ionic liquid are added respectively to the 50ml with stirring bar and condenser that fills 6ml water In a one-mouth bottle. Reflux reaction for 35 minutes under vigorous stirring, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, filtered with suction, washed the obtained filter residue with water, dried and recrystallized with methanol, vacuum After drying, pure 2-amino-7-hydroxy-3-cyano-4-(4-methoxyphenyl)-4H-chromene was obtained in 89% yield. The filtrate was directly added with p-methoxybenzaldehyde, malononitrile and resorcinol and reused.

[0026] 2-Amino-7-hydroxy-3-cyano-4-(4-methoxyphenyl)-4H-chromene: m.p.111~113℃; 1 HNMR (300MHz, acetone-d 6 ):δ=3.73(s, 3H, CH 3 ), 4.61(s, 1H, CH), 6.52(d, J=3.0Hz, 1H, ArH), 6.08(s,...

Embodiment 3

[0027]Embodiment 3: 10mmol o-chlorobenzaldehyde, 10mmol malononitrile, 10mmol resorcinol and 0.4mmol Bronster alkaline ionic liquid are added respectively to the 50ml single-necked bottle that has a stirring bar and a condenser tube filled with 6ml water middle. Under vigorous stirring, reflux reaction for 20 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, filtered with suction, the obtained filter residue was washed with water, dried and then recrystallized with methanol, vacuum After drying, pure 2-amino-7-hydroxy-3-cyano-4-(2-chlorophenyl)-4H-chromene was obtained in a yield of 93%. Add o-chlorobenzaldehyde, malononitrile and resorcinol directly to the filtrate and reuse it.

[0028] 2-amino-7-hydroxy-3-cyano-4-(2-chlorophenyl)-4H-chromene: m.p.185~187℃; 1 HNMR (300MHz, acetone-d 6 ): δ=5.24(s, 1H, CH), 6.17(s, 2H, NH 2 ), 6.48(d, J...

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Abstract

The invention discloses a method for preparing a 2-amido-4H-chromene derivative through green catalysis, and belongs to the technical field of organic chemical engineering. In the preparation reaction, the mole ratio of aromatic aldehyde to malononitrile to resorcinol is 1:1:1, the molar weight of an alkaline ion liquid catalyst accounts for 3%-5% of the molar weight of the used aromatic aldehyde, and the volume flow rate (ml) of reacted solvent water accounts for 40%-60% of the molar weight (mmol) of the aromatic aldehyde. The method comprises the following steps of carrying out reflux reaction for 15-45 minutes; after the reaction is finished, cooling to room temperature to separate a large quantity of solids; grinding the solids; standing; carrying out suction filtration; washing and drying obtained filter residues, and then recrystallizing by using methanol; carrying out vacuum drying to obtain a pure 2-amido-4H-chromene derivative. Compared with other preparation methods which take alkaline ion liquid as a catalyst, the method disclosed by the invention has the advantages of good catalytic activity, economic catalyst synthesis process and simple, convenient and economic whole preparation process, and is easy to biodegrade and convenient for industrialized large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and in particular relates to a green catalytic method for preparing 2-amino-4H-chromene derivatives. Background technique [0002] 2-Amino-4H-chromene is a very important class of organic compounds, it is the structural unit of many natural compounds, and its derivatives have a wide range of biological and pharmacological activities, such as antimicrobial, antiviral, mutagenic, anti Proliferation, sex hormones, and central nervous system activity. In addition, it can also be used as cosmetics, dyes and biodegradable pesticides, etc. Such compounds are usually prepared by a three-component one-pot reaction of aromatic aldehydes, active methylene compounds, and phenols. However, traditional catalysts generally have long reaction times, insufficient yields, use of volatile organic solvents, or cumbersome post-treatment. and other shortcomings. Therefore, developing a green, effi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58
CPCC07D311/58
Inventor 岳彩波高学频吴胜华诸荣孙
Owner ANHUI UNIVERSITY OF TECHNOLOGY