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Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex

A technology of naphthol aldehyde Schiff and Schiff base zirconium, which is applied in the field of preparation of new ionic β-naphthol aldehyde Schiff base zirconium complexes, achieving the effect of simple experimental operation

Active Publication Date: 2019-11-22
SHANXI MEDICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no public documents and patent applications about the preparation method of β-naphthol aldehyde Schiff base zirconium complex and the catalytic synthesis of 1,4-dihydropyridine derivatives at home and abroad.

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  • Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex
  • Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex
  • Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex

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preparation example Construction

[0031] Below in conjunction with concrete preparation example, the present invention will be further described:

[0032] 1. Synthesis of novel β-naphthol aldehyde Schiff base zirconium perfluoroalkane (benzene) sulfonic acid complexes

preparation example 1

[0034] Dissolve β-naphthol aldehyde Schiff base zirconium dichloride (1.0 mmol) in tetrahydrofuran (THF), N 2 Under protection, silver perfluorooctane sulfonate (2.0 mmol) was added and reacted for 1 h at room temperature in the dark. After filtration, add n-hexane to the filtrate until the layers are separated. Put it in the refrigerator for 24 hours, and a yellow solid was precipitated, with a yield of 80%.

preparation example 2

[0036] β-Naphthol aldehyde Schiff base zirconium dichloride (1.0 mmol) was dissolved in acetonitrile (CH 3 CN), N 2 Under protection, silver perfluorophenylsulfonate (2.0 mmol) was added, and the reaction was carried out at room temperature in the dark for 3 h. After filtration, add n-hexane to the filtrate until the layers are separated. Put it in the refrigerator for 24 hours, and a yellow solid was precipitated, with a yield of 70%.

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Abstract

The invention belongs to the technical field of catalytic organic synthesis, and particularly relates to a preparation method and application of a novel ionic beta-naphthol aldehyde Schiff base zirconium complex. Zirconium atoms are coordinated with a beta-naphthol aldehyde Schiff base ligand and water molecules, and two perfluoroalkyl (aryl) sulfonic acid groups are combined with central atom zirconium through covalent bonds and ionic bonds respectively. The preparation method comprises the following steps: dissolving beta-naphthol aldehyde Schiff base zirconium dichloride in a solvent, adding a silver salt under the protection of N2, reacting the mixture for 1-4 hours in a dark place at room temperature, performing filtration, adding n-hexane into filtrate until layering, putting the solution into a refrigerator, and freezing the solution for 24 hours to separate out the beta-naphthol aldehyde Schiff base zirconium complex. The beta-naphthol aldehyde Schiff base zirconium complex hashigh air stability and strong Lewis acidity, and can efficiently catalyze the Hantzsch reaction of aldehyde, beta-ketoester and ammonium acetate to synthesize 1,4-dihydropyridine derivatives.

Description

technical field [0001] The invention belongs to the technical field of catalytic organic synthesis, and in particular relates to a preparation method and application of a novel ionic β-naphthol aldehyde Schiff base zirconium complex. Background technique [0002] 1,4-Dihydropyridine compounds are nitrogen-containing heterocyclic compounds with extensive biological and pharmaceutical value. It is especially used clinically as a calcium ion channel blocker to treat diseases such as cardiovascular and cerebrovascular diseases and hypertension, and also plays an important role in anti-platelet aggregation, neuroprotection and anti-ischemia. The classic method of synthesizing 1,4-dihydropyridine compounds is through the Hantzsch reaction: that is, through the condensation reaction of one molecule of aldehyde, two molecules of β-ketoester and one molecule of ammonia. In recent years, exploring simple and efficient synthetic methods of 1,4-dihydropyridine compounds has become a ho...

Claims

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Application Information

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IPC IPC(8): C07F7/00B01J31/22C07D211/90
CPCC07F7/003B01J31/2217C07D211/90B01J2531/48
Inventor 李宁波王灵晓王静靳朝晖郝英健
Owner SHANXI MEDICAL UNIV
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