Synthesis method of difluoroalkyl substituted pyridone or pyrone

The technology of a difluoroalkyl group and a synthesis method is applied in the synthesis field of pyridone or pyranone, and achieves the effects that raw materials and reagents are simple and easy to obtain, the reaction is green and concise, and the dosage is small.

Inactive Publication Date: 2016-06-15
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention intends to provide a method for synthesizing difluoroalkyl-substituted pyridone or pyrone, so as to solve the defect that the prior art cannot efficiently and concisely synthesize difluoroalkyl-substituted pyridone or pyrone

Method used

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  • Synthesis method of difluoroalkyl substituted pyridone or pyrone
  • Synthesis method of difluoroalkyl substituted pyridone or pyrone
  • Synthesis method of difluoroalkyl substituted pyridone or pyrone

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preparation example Construction

[0033] The invention provides a method for synthesizing difluoroalkyl substituted pyridone or pyrone. Preferably, the method includes the steps of: in an inert solvent, under the irradiation of blue light or green light, using a complex containing iridium and ruthenium as a photocatalyst, the formula pyridone / pyrone (ie A, D or F) react with a compound of formula B) for a period of time (such as 1-36 hours) to form a difluoroalkyl substituted pyridone or pyrone (compound C, E or G);

[0034]

[0035] In various forms, R 1 , R 2 , R 3 , R 4 , R 5 , X is defined as mentioned above.

[0036] More preferably, said formula A, E, F compound is selected from the compound of following group:

[0037]

[0038] Wherein, the compound of formula B is preferably a compound selected from the following group:

[0039] ClCF 2 R 5 , BrCF 2 R 5 、ICF 2 R 5 .

[0040] In various forms, R 4 as above.

[0041] More preferably, the compound of formula B is a compound selected f...

Embodiment 1

[0055]

[0056] Into a 25mL reaction tube, add 1.3mg (0.5mol%) Ir(PPy) 3 , K 2 HPO 4 (0.8mmol), compound A-1 (0.4mmol, 1 equivalent), after nitrogen replacement three times, add 3mL dimethylsulfoxide (DMSO), inject 100μL (0.80mmol) compound B-1, stir under blue light irradiation for 24 hours , to obtain compound C-1. The yield was 84%.

[0057] 1 HNMR (400MHz, CDCl 3 )δ8.11(s, 1H), 7.64(t, J=7.2Hz, 2H), 7.37(d, J=8.8Hz, 1H), 7.29(t, J=7.4Hz, 1H), 4.37(q, J=7.2Hz, 2H), 3.67(s, 3H), 1.33(t, J=7.2Hz, 3H). 19 FNMR (376MHz, CDCl 3 )δ-109.5(s,2F). 13 C-NMR (100MHz, CDCl 3 )δ163.1(t, J=32.6Hz), 159.2(t, J=4.4Hz), 140.2, 137.3(t, J=7.1Hz), 132.3, 130.0, 124.7(t, J=24.1Hz), 122.8 , 118.7, 114.2, 111.2 (t, J = 247.6 Hz), 62.9, 29.2, 13.8.

Embodiment 2

[0059]

[0060] Into a 25mL reaction tube, add 1.3mg (0.5mol%) Ir(PPy) 3 , K 2 HPO 4 (0.8mmol), compound A-1 (0.4mmol, 1 equivalent), after nitrogen replacement three times, add 3mL dimethylsulfoxide (DMSO), inject 100μL (0.80mmol) compound B-1, and stir for 24 hours under green light irradiation Finally, compound C-1 was obtained. The yield was 50%.

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Abstract

The invention discloses a method for synthesizing difluoroalkyl substituted pyridone or pyrone under simple conditions. Specifically, starting from simple pyridones, pyrones, and halogenated difluoroalkyl compounds (chloro, bromo, iodo), under light conditions, complexes with iridium or ruthenium as the core act as catalysts , A method for obtaining various difluoroalkyl-substituted pyridones or pyrones in high yields. The method uses simple and easy-to-obtain pyridones and pyrones and halogenated difluoroalkyl compounds (chloro, bromo, iodo) as raw materials, and has the advantages of less catalyst consumption, wide application range of substrates, easy operation and fast reaction. High efficiency and other advantages. The obtained structures are some important fluorine-containing building blocks at present, and have great application prospects in the field of biomedicine.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing difluoroalkyl-substituted pyridone or pyrone. Background technique [0002] Pyridone and pyrone are a class of very important structural units, which have a very wide and important application in biomedicine, and are one of the parent core structures with the most potential for drug-making. On the one hand, its chemical properties are stable and there are many sites available for modification. [0003] [0004] On the other hand, due to the special properties of fluorine atoms and fluorine-containing groups (such as: small atomic radius of fluorine atoms, high electronegativity, and high lipophilicity of fluorine-containing groups, etc.), fluorine-containing compounds are widely used in the field of medicine. Widespread concern. According to statistics, fluorine-containing drugs account for more than 20% of the whole drug; however, unfortunately, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227C07D213/64C07D215/233C07D311/12C07D311/16
CPCC07D215/227C07D213/64C07D215/233C07D311/12C07D311/16
Inventor 贺春阳李晓飞
Owner ZUNYI MEDICAL UNIVERSITY
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