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A kind of preparation method of thiazolo[3,2-α]pyridine derivatives and its preparation catalyst

A technology for thiazolo and derivatives, applied in the field of organic chemical industry, can solve the problems of poor product yield stability, few cycles of use, large catalyst loss, etc., and achieves the effects of reduced preparation cost, low activity loss, and easy separation

Active Publication Date: 2018-11-16
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

[0006] The purpose of the present invention is to overcome the large amount of catalyst loss that exists in the process of utilizing alkaline ionic liquids to catalyze the preparation of thiazolo[3,2-α]pyridine derivatives in the prior art, the number of times of recyclable use is less, and the loss of the resulting product Due to the relatively poor yield stability, a preparation method of thiazolo[3,2-α]pyridine derivatives and a loaded alkaline ionic liquid catalyst for its preparation are provided, and the catalyst of the present invention is used to catalyze the preparation of thiazolo[3,2-α]pyridine derivatives. [3,2-α]pyridine derivatives, the loss of the catalyst during recycling is extremely low, the number of times of recycling is large, and the yield of the obtained product is relatively stable

Method used

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  • A kind of preparation method of thiazolo[3,2-α]pyridine derivatives and its preparation catalyst
  • A kind of preparation method of thiazolo[3,2-α]pyridine derivatives and its preparation catalyst
  • A kind of preparation method of thiazolo[3,2-α]pyridine derivatives and its preparation catalyst

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Experimental program
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Effect test

Embodiment 1

[0038] 10mmol benzaldehyde, 10mmol malononitrile, 5mmol methyl thioglycolate and 1.60g magnetic material supported alkaline ionic liquid catalyst are added respectively to the 250ml single-necked round bottom flask with stirring bar and condenser tube that fills 20ml 95% ethanol aqueous solution middle. Heat to reflux for 17 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, the catalyst is adsorbed by a magnet while it is hot, the remaining reaction solution is cooled to room temperature, filtered with suction, the filter residue is washed with 95% ethanol aqueous solution, and vacuum-dried to obtain 5-amino -2,3-dihydro-3-oxo-7-phenyl-2-(benzylidene)-7H-thiazolo[3,2-α]pyridine-6,8-dicarbonitrile, the yield is 94%. Put the adsorbed catalyst into the reaction solution composed of 20ml filter residue washing solution and filtrate, and directly add benzaldehyde, malononitrile and methyl thioglycolate for repeated use.

[0039] The 5-amino-2,...

Embodiment 2

[0041] 10mmol benzaldehyde, 10mmol ethyl cyanoacetate, 5mmol methyl mercaptoacetate and 2.00g magnetic material loaded alkaline ionic liquid catalyst were added respectively to the 250ml single-mouth circle with stirring bar and condensing tube filled with 20ml 97% ethanol aqueous solution in the bottom flask. Heated to reflux for 23 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, the catalyst was adsorbed by a magnet while it was hot, the remaining reaction solution was cooled to room temperature, filtered with suction, the filter residue was washed with 97% ethanol aqueous solution, and vacuum dried to obtain (E) -Diethyl-5-amino-2-benzylidene-3-oxo-7-phenyl-3,7-dihydro-2H-thiazolo[3,2-α]pyridine-6,8- Dinitrile, the yield is 91%, and the selectivity is 100%. Put the adsorbed catalyst into the reaction liquid composed of 20ml filter residue washing liquid and filtrate, and directly add benzaldehyde, ethyl cyanoacetate and methyl thiogl...

Embodiment 3

[0044] 10mmol p-tolualdehyde, 11mmol malononitrile, 5mmol methyl thioglycolate and 1.80g magnetic material loaded alkaline ionic liquid catalyst were added respectively to the 250ml single port with stirring bar and condenser tube filled with 25ml 96% ethanol aqueous solution in a round bottom flask. Heat to reflux for 24 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, the catalyst is adsorbed by a magnet while it is hot, the remaining reaction solution is cooled to room temperature, suction filtered, the filter residue is washed with 96% ethanol aqueous solution, and vacuum-dried to obtain 5-amino -2,3-Dihydro-7-(4-methylphenyl)-2-[(4-methylphenyl)methylene]-3-oxo-7H-thiazolo[3,2-α]pyridine-6 , 8-dinitrile, the yield was 96%. Put the adsorbed catalyst into the reaction solution composed of 25ml filter residue washing solution and filtrate, and directly add p-tolualdehyde, malononitrile and methyl thioglycolate for repeated use.

[0045...

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Abstract

The invention discloses a method and a catalyst for preparing thiazolo [3, 2-alpha] pyridine derivatives, and belongs to the technical field of organic chemical industry. Magnetic material loaded alkaline ionic liquid is used as the catalyst, a molar ratio of aromatic aldehyde to active methylene compounds to methyl thioglycolate in preparation reaction is 2:(2-2.5):1, the molar weight, which is computed on the basis of alkaline ionic liquid on load, of the magnetic material loaded alkaline ionic liquid, which is the catalyst, is 8-12% of the molar weight of the methyl thioglycolate, and the reflux reaction time is 17-67 min. Compared with other preparation methods, the method and the catalyst have the advantages that the catalyst is low in loss during recycling and is high in recyclable times and product selectivity, integral preparation procedures are simple, convenient and economical, and accordingly industrial large-scale production can be facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and in particular relates to a preparation method of thiazolo[3,2-α]pyridine derivatives and a loaded alkaline ionic liquid catalyst for the preparation thereof. 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: can effectively inhibit the formation of β-amyloid protein and CDK2 protein, and can be used as α-glucose Glycolic acid inhibitor, also has 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 simpl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04B01J31/02
CPCB01J31/0284B01J31/0295C07D513/04
Inventor 沈建忠沈智培
Owner 东营睿港投资服务有限责任公司