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A green catalytic method for preparing thiazolo[3,2-α]pyridine derivatives

A technology for catalytic preparation of thiazolides, which is applied in organic chemistry and other fields, can solve the problems of large usage and loss, and achieve the effects of high alkalinity, simple preparation process and good catalytic activity

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

[0004] The purpose of the present invention is to overcome the use of alkaline ionic liquids in the prior art to prepare thiazolo[3,2-α]pyridine derivatives in the process of using a large amount of ionic liquids and a large loss in recycling. To overcome the shortcomings of organic solvents, and provide a Bronster alkaline ionic liquid that is easy to biodegrade, has high alkalinity and high catalytic efficiency as a green catalyst, and catalyzes the preparation of thiazolo[3,2-α] under the condition of water as a solvent Method for Pyridine Derivatives

Method used

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  • A green catalytic method for preparing thiazolo[3,2-α]pyridine derivatives
  • A green catalytic method for preparing thiazolo[3,2-α]pyridine derivatives
  • A green catalytic method for preparing thiazolo[3,2-α]pyridine derivatives

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Experimental program
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Effect test

Embodiment 1

[0019] 10mmol benzaldehyde, 10mmol malononitrile, 5mmol methyl thioglycolate and 0.15mmol Bronsted basic ionic liquid were respectively added to 50ml single-necked bottles with a stirring bar containing 15ml water. Vigorously stir the reaction at room temperature for 23 minutes, TLC (thin plate chromatography) detection, the raw material point disappears (reaction is over), a large amount of solids are precipitated, crush the solids, let stand, and filter with suction, the obtained filter residue is washed with water, dried and then recrystallized with absolute ethanol , after vacuum drying to obtain pure 5-amino-2,3-dihydro-3-oxo-7-phenyl-2-(benzylidene)-7H-thiazolo[3,2-α]pyridine-6 , 8-dinitrile, the yield was 94%. The filtrate was directly added with benzaldehyde, malononitrile and methyl thioglycolate for repeated use.

[0020] 5-Amino-2,3-dihydro-3-oxo-7-phenyl-2-(benzylidene)-7H-thiazolo[3,2-α]pyridine-6,8-dicarbonitrile: m.p.247~249℃; 1 HNMR (500MHz, DMSO-d 6 ): δ=4...

Embodiment 2

[0022] 10mmol of p-tolualdehyde, 10mmol of malononitrile, 5mmol of methyl thioglycolate and 0.18mmol of Brönstedt basic ionic liquid were respectively added to 50ml single-necked bottles containing 15ml of water with a stirring bar. Vigorously stir the reaction at room temperature for 27 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, a large amount of solid precipitates, crush the solid, stand still, filter with suction, the obtained filter residue is washed with water, dried and recrystallized with absolute ethanol, after vacuum drying Pure 5-amino-2,3-dihydro-7-(4-tolyl)-2-[(4-tolyl)methylene]-3-oxo-7H-thiazolo[3,2- α]pyridine-6,8-dicarbonitrile, the yield is 95%. The filtrate was directly added with p-tolualdehyde, malononitrile and methyl thioglycolate for repeated use.

[0023] 5-Amino-2,3-dihydro-7-(4-methylphenyl)-2-[(4-methylphenyl)methylene]-3-oxo-7H-thiazolo[3,2-α] Pyridine-6,8-dicarbonitrile: m.p.239~240℃; 1 HNMR (500MHz, D...

Embodiment 3

[0025] 10mmol p-methoxybenzaldehyde, 15mmol malononitrile, 5mmol methyl thioglycolate and 0.20mmol Bronsted basic ionic liquid were respectively added to 100ml single-necked bottles with stirring bars containing 20ml water. Vigorously stir the reaction at room temperature for 53 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, a large amount of solid precipitates, crush the solid, stand still, and filter with suction, the obtained filter residue is washed with water, dried, and recrystallized with absolute ethanol, after vacuum drying Pure 5-amino-2,3-dihydro-7-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methylene]-3-oxo-7H-thiazolo[ 3,2-α]pyridine-6,8-dicarbonitrile, the yield was 87%. The filtrate was directly added with p-methoxybenzaldehyde, malononitrile and methyl thioglycolate for repeated use.

[0026] 5-amino-2,3-dihydro-7-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methylene]-3-oxo-7H-thiazolo[3, 2-α]pyridine-6,8-dicarbonitrile: m.p.242~24...

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Abstract

The invention discloses a green catalysis preparation method of a thiazole [3,2-alpha] pyridine derivative, and belongs to the technical field of organic chemical industry. In preparation reaction, the mole ratio of aromatic aldehyde to malononitrile to methyl thioglycolate is 2:(2-4):1, and the mole of a Bronsted alkaline ionic liquid catalyst accounts for 3%-5% that of methyl thioglycolate. The method comprises the following steps: reacting for 20-65 minutes at room temperature, cooling to room temperature to separate out a large quantity of solids, grinding the solids, standing, performing suction filtration, washing a residue with water, drying, recrystallizing with absolute ethyl alcohol, and performing vacuum drying to obtain the pure thiazole [3,2-alpha] pyridine derivative. Compared with other traditional preparation methods with alkali or an alkaline ionic liquid as a catalyst, the green catalysis preparation method has the advantages that the catalytic activity is good, the use amount of the catalyst and the loss amount of the catalyst in reuse are low, the catalyst can be easily degraded biologically, the whole preparation process is simple and convenient, and industrial large-scaled production can be achieved conveniently.

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 thiazolo[3,2-α]pyridine derivatives. Background technique [0002] Thiazolo[3,2-α]pyridine derivatives are a very important class of organic compounds, which have very significant physiological activities, such as being able to effectively inhibit the formation of β-amyloid protein and CDK2 protein, and can be used as α-glucoglycoside Enzyme inhibitors and antibacterial and antifungal activities. Therefore, it is of great significance to study the synthesis of thiazolo[3,2-α]pyridine derivatives. However, the traditional preparation methods of thiazolo[3,2-α]pyridine derivatives generally have disadvantages such as long reaction time, poisonous and harmful catalyst, large usage amount and non-recyclable use. Therefore, developing a green, efficient and simple method for synthesizing thiazolo[3,2-α]pyridine der...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 岳彩波杜勤杰吴胜华陆良俊诸荣孙朱琳
Owner ANHUI UNIVERSITY OF TECHNOLOGY