2-hydroxypyridine compound and its synthesis method

A technology of hydroxypyridine and synthesis method, applied in the direction of organic chemistry, organic chemistry, etc., to achieve the effects of wide applicability, easy price, and simple and mild synthesis reaction conditions

Active Publication Date: 2022-04-29
NANJING TECH UNIV
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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 its synthesis method
  • 2-hydroxypyridine compound and its synthesis method
  • 2-hydroxypyridine compound and its synthesis method

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 2-hydroxypyridine compounds, their synthesis method and application. Using enaminone as a starting material and tempo salt as an oxidizing agent, 2-hydroxypyridine compounds are generated through oxidation reaction and coupling cyclization reaction under heating conditions. The reaction has strong functional group compatibility, the yield is as high as 80%, and the product has functional group diversity. It can be used as a precursor for organic synthesis, and the 2-position hydroxyl group and 6-position hydrogen atom in the structure can be further functionalized to obtain drug molecular skeletons or compounds with potential biological activity.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/76C07D409/06
CPCC07D211/76C07D409/06C07B2200/07
Inventor 黄菲李明瑞孙一斐于杨
Owner NANJING TECH UNIV
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