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Method for synthesizing heteroaryl methylamine compound through oxidation reduction-decarboxylation coupled reaction

A heteroaryl methylamine, decarboxylation coupling technology, applied in the direction of organic chemistry, etc., to achieve the effect of low production cost, convenient operation, and less environmental pollution

Pending Publication Date: 2021-02-05
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is of great biological significance to modify the active site of N-(heteroarylmethyl)-arylamine derivatives. The five-membered heterocyclic aromatic amine derivatives N α The redox-decarboxylation coupling reaction of NHP esters has not been reported

Method used

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  • Method for synthesizing heteroaryl methylamine compound through oxidation reduction-decarboxylation coupled reaction
  • Method for synthesizing heteroaryl methylamine compound through oxidation reduction-decarboxylation coupled reaction
  • Method for synthesizing heteroaryl methylamine compound through oxidation reduction-decarboxylation coupled reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Synthesis of N-(cyclohexyl(5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-4-methylaniline

[0031]

[0032] Add magnetons to a dry 10mL reaction tube, followed by N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)4-methylaniline (0.2mmol) And cyclohexane NHP ester (0.3mmol), copper acetylacetonate (10 mol%, 0.02mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mol%, 0.03mmol) , (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15 mol%, 0.03mmol) and triethylenediamine (0.4mmol, 2.0 equiv) , then pump out the air and backfill with Ar (3 times). Acetonitrile (2 mL) was added, the reaction tube was transferred to a blue light reactor (6 W) and irradiated there for 12 h. The solvent was distilled off under reduced pressure and separated by column chromatography (silica gel: 200-300 mesh, eluent volume ratio: n-hexane:ethyl acetate=15:1). The solvent was distilled off under reduced pressure to obtain a white solid product, namely N-(cyclohexyl(5-phenyl-1,3,4-oxadiazol...

Embodiment 2

[0034] Example 2: Synthesis of N-(cyclohexyl(5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-4-methoxyaniline:

[0035]

[0036] Add magnetons to a dry 10mL reaction tube, followed by adding N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)4-methoxyaniline (0.2mmol ) and cyclohexane NHP ester (0.3mmol), copper acetylacetonate (10 mol%, 0.02mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mol%, 0.03mmol ), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15 mol%, 0.03mmol) and triethylenediamine (0.4mmol, 2.0 equiv ), then evacuated and backfilled with Ar (3 times). Acetonitrile (2 mL) was added, the reaction tube was transferred to a blue light reactor (6 W) and irradiated there for 12 h. The solvent was distilled off under reduced pressure and separated by column chromatography (silica gel: 200-300 mesh, eluent volume ratio: n-hexane:ethyl acetate=15:1). The solvent was distilled off under reduced pressure to obtain a white solid product, namely N-(cyclohexyl(5-phenyl-1,3,4-o...

Embodiment 3

[0038] Embodiment 3: the synthesis of N-(benzo[d]oxazol-2-yl(cyclohexyl)methyl)-4-methylaniline

[0039]

[0040] Add magnetons to a dry 10mL reaction tube, followed by sequential addition of N-(benzo[d]oxazol-2-ylmethyl)-4-methylaniline (0.2mmol) and cyclohexane NHP ester (0.3 mmol), copper acetylacetonate (10 mol%, 0.02mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mol%, 0.03mmol), (9,9-dimethyl yl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15 mol%, 0.03 mmol) and triethylenediamine (0.4 mmol, 2.0 equiv), then evacuate the air and backfill with Ar (3 times). Acetonitrile (2 mL) was added, the reaction tube was transferred to a blue light reactor (6 W) and irradiated there for 12 h. The solvent was distilled off under reduced pressure and separated by column chromatography (silica gel: 200-300 mesh, eluent volume ratio: n-hexane:ethyl acetate=15:1). The solvent was distilled off under reduced pressure to obtain a white solid product, namely N-(benzo[d]oxazol-2-yl(...

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Abstract

The invention provides a method for synthesizing a heteroaryl methylamine compound through an oxidation-reduction decarboxylation coupled reaction. The method comprises the following steps: in an organic solvent and with an N-(heteroarylmethyl)-arylamine derivative and NHP ester as raw materials and a double-ligand complex of copper salt as a catalyst, adding an additive, conducting reacting at room temperature for 12-24 hours under the protection of argon and in the presence of blue light, carrying out reduced-pressure distillation to remove the solvent after the reaction is completed, and carrying out column chromatographic separation to obtain the target product. According to the method, the oxidation reduction-decarboxylation coupled reaction of the alpha position of a five-membered aromatic heterocycle and the NHP ester is realized for the first time, a reaction reagent is low in price, reaction conditions are mild, a photocatalyst is not needed, yield is high, the purity of the product is good, and post-treatment is simple; and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing heteroarylmethylamine compounds, in particular to a method for synthesizing heteroarylmethylamine compounds through oxidation-reduction-decarboxylation coupling reaction, and belongs to the technical field of chemical synthesis. Background technique [0002] Compounds containing heterocyclic structures have been attracting attention due to their wide range of biological activities, among which five-membered nitrogen heterocyclic rings are widely used because of their unique biological activities, especially 1,3,4 with unique anti-inflammatory activities - Compounds of oxadiazole nucleus, oxadiazole molecules containing substituents also have other important biological activities, such as analgesic, antibacterial, anticonvulsant, antihypertensive, can be used as enzyme inhibitors and muscle glycogen phosphorylase Inhibitors. In the study of cholesteryl ester transfer protein (CETP) inhibitory activity,...

Claims

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Application Information

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IPC IPC(8): C07D271/10C07D263/56C07D235/14C07D263/32C07D277/28
CPCC07D271/10C07D263/56C07D235/14C07D263/32C07D277/28
Inventor 霍聪德牛鹏飞
Owner NORTHWEST NORMAL UNIVERSITY
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