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A system and method for preparing 6-mercapto polysubstituted pyridine derivatives by three-component one-pot reaction

A derivative and three-component technology, which is applied in the system field of preparing 6-mercapto polysubstituted pyridine derivatives by three-component one-pot reaction, can solve the problem of poor catalytic effect or catalytic effect, low economic benefit, poor universality, etc. The problem is to solve the large amount of catalyst used, reduce the production cost, and improve the catalytic activity.

Active Publication Date: 2019-09-17
东营睿港投资服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the characteristics of easy biodegradation of the catalyst and simple product purification process, but the reaction operation process is still complicated, the reactants need to be added in batches, and has the disadvantages of large catalyst usage, long reaction time, and low product yield. Therefore, In the process of large-scale industrial production, its economic benefit is low
In addition, the universality of this method is relatively poor, and the catalyst in the reaction has no catalytic effect or poor catalytic effect on the reaction raw materials with weak reactivity, that is, the optional range of reaction raw materials is narrow

Method used

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  • A system and method for preparing 6-mercapto polysubstituted pyridine derivatives by three-component one-pot reaction
  • A system and method for preparing 6-mercapto polysubstituted pyridine derivatives by three-component one-pot reaction
  • A system and method for preparing 6-mercapto polysubstituted pyridine derivatives by three-component one-pot reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0046] 1mmol 2,6-dichlorobenzaldehyde, 2mmol malononitrile, 1mmol thiophenol and 0.03mmol high-efficiency alkaline ionic liquid catalyst are respectively added to the raw material mixing device with reflux device of 9ml 96% ethanol aqueous solution , the reaction system was fully mixed by stirring with a stirrer, the raw material mixing device was placed in a microwave reaction device, and the reaction device was set to 300W for reaction, and the reaction was followed by TLC, and the reaction was completed in 8 minutes. After cooling to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction, and the resulting filter residue was washed with 96% ethanol aqueous solution (3ml×3 times), and dried in vacuo to obtain 2-amino-4-(2,6-dichloro Phenyl)-6-phenylthio-1,4-dihydro-pyridine-3,5-dicarbonitrile, the yield was 96%. The filtrate after filling up 9ml with the washing solution was directly added with 2,6-dichlorobenzalde...

Embodiment 2

[0053] The preparation process of this embodiment is basically the same as that of Example 1, the only difference being that the power of microwave heating controlled in this embodiment is 250W, and the reaction time is 12min. As a result, the obtained 2-amino-4-(2,6-dichloro The yield of phenyl)-6-phenylthio-1,4-dihydro-pyridine-3,5-dicarbonitrile was 83%.

Embodiment 3

[0055] The preparation process of this embodiment is basically the same as that of Example 1, the only difference being that the microwave heating power is controlled to be 350W in this embodiment, and the obtained 2-amino-4-(2,6-dichlorophenyl)-6 The yield of -thiophenyl-1,4-dihydro-pyridine-3,5-dicarbonitrile was 87%.

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Abstract

The invention discloses a system and method for preparing a 6-mercapto polysubstituted pyridine derivative through a three-component one-pot reaction, belonging to the technical field of organic synthesis. The preparation system for the 6-mercapto polysubstituted pyridine derivative comprises a raw material mixing device, a microwave reaction device, a suction filtration device, a washing device and a vacuum drying device which are sequentially arranged, wherein the microwave reaction device is used for a microwave heating reaction of raw materials in the raw material mixing device; the suction filtration device is used for suction filtration of a reaction product; the washing device and the vacuum drying device are used for washing and vacuum drying of a filter residue obtained after filtering, respectively. According to the invention, aromatic aldehydes, malononitrile and mercapto compounds are used as reaction materials, and the 6-mercapto polysubstituted pyridine derivative is prepared under the catalysis of an alkaline ionic liquid catalyst. The catalyst used in the invention is high in catalytic activity and low in usage amount and cyclic loss; and the prepared derivate has high yield and high purity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a system and method for preparing 6-mercapto multi-substituted pyridine derivatives by a three-component one-pot reaction. Background technique [0002] Pyridine skeleton is a very important heterocyclic structure, which widely exists in biologically active compounds in nature, and can be applied to drug molecules, functional ligands, intermediates, and the construction of multi-substituted structural molecules. The multi-substituted pyridine derivatives that first appeared in the 1960s can be used in herbicides, insecticides, etc., such as picloram, triclopyr, fluoride, etc. Disulfuron etc. In addition, the 6-substituted mercapto multi-substituted pyridine derivative obtained after introducing a mercapto group at the 6-position of the multi-substituted pyridine ring has antiviral, antitumor, antibacterial, anticancer virus and other activities. Theref...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/85
Inventor 沈建忠卢华
Owner 东营睿港投资服务有限责任公司
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