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2-hydroxypyridine compound and synthesis method thereof

A technology of hydroxypyridine and synthesis method, which is applied in the direction of organic chemistry, organic chemistry, etc., to achieve the effects of good functional group tolerance, strong functional group compatibility, and wide applicability

Active Publication Date: 2021-04-02
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current synthetic methods are: (1) condensation reaction of aldehyde, β-ketoester and ammonia (Hantzsch dihydropyridine synthesis method); (2) condensation reaction of aldehyde and ammonia (Chichibabin pyridine synthesis reaction); (3) cyano Condensation reaction of acetate, 1,3-diketone and ammonia (Guareschi-Thorpe condensation reaction); (4) Cycloaddition reaction of azadienes and dienophiles (Hetero-Diels-Alder reaction), with The synthesis of polysubstituted pyridines with enaminones as the starting material has not been reported yet

Method used

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  • 2-hydroxypyridine compound and synthesis method thereof
  • 2-hydroxypyridine compound and synthesis method thereof
  • 2-hydroxypyridine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] Weigh 3-(benzylamino)-1-(4-chlorophenyl)-2-methylprop-2-en-1-one 2a (0.6mmol) into a 25mL Schlenk reaction flask, add 6mL of DCM, at 40°C Stir in an oil bath for 2 minutes, add Tempo salt 3a (0.6 mmol), and react for 1 h. After the reaction, the mixture was cooled to room temperature, extracted with dichloromethane and water, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum Ether (60-90°C) / ethyl acetate, v / v=10:1), the target product 1a-α (75mg, yield 58%), 1a-β (23mg, yield 17%) was obtained as colorless oil , dr:77:23. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0047]

[0048] Weigh 3-(benzylamino)-1-(4-methylphenyl)-2-methylprop-2-en-1-one 2b (0.6mmol) into a 25mL Schlenk reaction flask, add 2mL of toluene, and Stir in an oil bath for 2 minutes, add Tempo salt 3b (0.7 mmol), and react for 0.2 h. After the reaction, the mixture was cooled to room temperature, extracted with dichloromethane and water, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum Ether (60-90°C) / ethyl acetate, v / v=10:1), the target product 1b-α (73mg, yield 55%), 1b-β (25mg, yield 20%) was obtained as colorless oil , dr:74:26. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0050]

[0051]Sequentially weigh 3-(benzylamino)-1-(4-methoxyphenyl)-2-methylprop-2-en-1-one 1-ketone-1-phenyl-3-benzylamino-2 - Propylene 2c (0.6mmol) in a 25mL Schlenk reaction flask, add DMSO 2mL, stir in an oil bath at 80°C for 2 minutes, add Tempo salt 3c (0.6mmol), and react for 0.5h After the reaction is over, the mixture is cooled to At room temperature, dichloromethane and water were extracted, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / Ethyl acetate, v / v=10:1), the target product 1c (112 mg, yield 80%, dr:95:5) was obtained as a colorless oil. The target product was confirmed by NMR and high-resolution mass spectrometry.

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Abstract

The invention discloses a 2-hydroxypyridine compound and a synthesis method and application thereof. According to the method, enaminone is used as a starting raw material, tempo salt is used as an oxidizing agent, and the 2-hydroxypyridine compound is generated through an oxidation reaction and a coupling cyclization reaction under a heating condition. The reaction functional group is high in compatibility, the yield is as high as 80%, and the product has functional group diversity. The compound can be used as an organic synthesis precursor, and 2-hydroxyl and 6-hydrogen atoms in the structurecan be further functionalized to obtain a drug molecular skeleton or a compound with potential biological activity and the like.

Description

technical field [0001] The invention relates to chemical industry and medicine, in particular to unsaturated nitrogen-containing heterocyclic compound 2-hydroxypyridine compound and its synthesis method. Background technique [0002] Pyridine is an important skeleton structure of many natural products, and it is also an important class of compounds in drug research. As a structural unit, pyridine is one of the foundations of biochemistry. Because of its special structure, it is prone to nucleophilic substitution reactions, and because it contains nitrogen atoms, it has a certain degree of basicity and can interact with many organisms through hydrogen bonds. Molecules work. These characteristics make it play an important role in synthetic drugs and chemical agents, and have antihypertensive, antithrombotic, anti-inflammatory, anti-tuberculosis, anticonvulsant, anti-HIV, analgesic, antibacterial, and insecticidal effects (Eur.J. Pharmacol.2002 441, 203; Eur.J.Med.Chem.2014, ...

Claims

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Application Information

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IPC IPC(8): C07D211/76C07D409/06
CPCC07D211/76C07D409/06C07B2200/07
Inventor 黄菲李明瑞孙一斐于杨
Owner NANJING UNIV OF TECH
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