Multi-substituted fluorine-containing pyridine

A multi-substituted, pyridine technology, applied in the multi-substituted pyridine and synthesis fields, can solve the problems of difficulty in introducing fluorine atoms and not many fluorine-containing pyridines.

Inactive Publication Date: 2010-08-11
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although a large number of methods for synthesizing various substituted pyridines have been reported in the literature, there are not many methods for synthesizing fluorine-containing pyridines, because it is generally more difficult to introduce fluorine atoms on heterocycles than on corresponding benzene rings, and the development of New pyridine syntheses are also necessary

Method used

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  • Multi-substituted fluorine-containing pyridine
  • Multi-substituted fluorine-containing pyridine
  • Multi-substituted fluorine-containing pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Experimental procedure

[0052] Add alkynyl imine 1 (0.4 mmol) into a solution of tetrahydrofuran (2 mL) dissolved with 3 equivalents of methylamine 2 and 2.5 equivalents of cesium carbonate at 80°C for 2-7 hours (24 hours for 1e). Monitor the response. After the reaction, the reaction solution was directly filtered, the filtrate was spin-dried, and the residue was subjected to column chromatography to obtain product 3.

[0053] Compound data

[0054] 1.3-fluoro-N,2,6-triphenylpyridin-4-amine

[0055] 3-fluoro-4-phenylamino-2,6-diphenylpyridine (3a)

[0056]

[0057] White solid, melting point 127-129°C; 1 H NMR (300MHz, CDCl 3 )δ8.02(d, J=7.1Hz, 2H), 7.95(d, J=7.6Hz, 2H), 7.56-7.14(m, 12H), 6.34(d, J=3.3Hz, 1H); 19 F NMR (282MHz, CDCl 3 )δ-152.37; 13 C NMR (100MHz, CDCl 3 )δ153.3(d, J=5.9Hz), 146.9(d, J=253.1Hz), 144.0(d, J=8.1Hz), 140.6(d, J=10.2Hz), 139.5, 139.2, 136.0(d , J=5.1Hz), 129.8, 129.0, 129.0 (d, J=5.9Hz), 128.7, 128.6, 128.4, 127.0, 124.7, 122...

Embodiment 2

[0139] Experimental procedure

[0140] The alkynyl imine 1 (0.4 mmol) was added into a tetrahydrofuran solution (2 mL) dissolved with 2.0 equivalent of n-butylamine to react at 80°C for 2 hours, and the reaction was monitored by thin-layer chromatography. After the reaction, the reaction solution was directly spin-dried, and then the intermediate 4v was obtained through column chromatography. Dissolve it in 2 ml of anhydrous tetrahydrofuran, add sodium hydride at room temperature, then slowly raise the temperature to 80°C, react for about 20 minutes, quench with ice water, then separate, dry, and column chromatography to obtain Product 3v.

[0141] Compound data

[0142] 22.3-fluoro-N, 6-diphenyl-2-propylpyridin-4-amine

[0143] 3-Fluoro-4-phenylamino-6-phenyl-2-propylpyridine (3v)

[0144]

[0145] yellow liquid; 1 H NMR (300MHz, CDCl 3 )δ7.81 (d, J=2.9Hz, 2H), 7.43-7.03 (m, 9H), 6.23 (s, 1H), 2.90-2.79 (m, 2H), 1.92-1.75 (m, 2H), 1.04 (t, J=7.4Hz, 3H); 19 F NMR (2...

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Abstract

The invention relates to multi-substituted pyridine, in particular to multi-substituted fluorine-containing pyridine which is obtained by performing the reaction of alkynyl imine and benzylamine for 1 to 30h at 60 to 100 DEG C in an organic solvent in the presence of alkali. Various multi-substituted 3-hydrogen, 3-fluorine and 3-trifluoromethyl pyridine derivatives can be synthesized through a cascade reaction of fluoroalkyl alkynyl imine and methylamine. Substituent groups on pyridine rings can be introduced step by step from a very beginning raw material preparation step, and various compounds with bioactivities synthesized by adopting the method can be used for synthesizing insecticides and antibacterial drugs.

Description

technical field [0001] The invention relates to a multi-substituted pyridine and a new synthesis method, in particular to a new synthesis method of a multi-substituted fluorine-containing pyridine. Background technique [0002] The pyridine ring structure widely exists in natural compounds and bioactive molecules. Compounds containing this structure may be used as anticancer drugs, antibacterial drugs, antiviral drugs or as pesticides. The pyridine ring is also the core of many widely used ligands Structure. Therefore, a series of pyridine derivatives were synthesized to study the relationship between their structure and activity and to develop more active pyridine analogs. It is well known that the introduction of fluorine atoms or fluorine-containing groups in organic molecules will completely change its chemical, physical and biological properties, so by introducing fluorine elements on the pyridine ring, perhaps the inventors will obtain some useful compounds or material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D409/04C07D213/79C07D213/803C07D405/04
Inventor 吴永明陈资衔
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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