Synthetic method of nitrogen-containing heterocyclic ferrocene derivatives

A technology for ferrocene derivatives and synthesis methods, which is applied in the field of synthesis of nitrogen-containing heterocyclic ferrocene derivatives, can solve problems such as difficult industrial production and application, hazards, and strict requirements for reagents and equipment, and achieve easy access, The effect of stable process and low production cost

Active Publication Date: 2020-08-25
FOSHAN ENANTIOSIC CORP LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A small amount of research involves the substitution of nitrogen-containing heterocyclic ferrocene as the core structure, but the synthetic route has strict requirements on reagents and equipment, requiring the use of highly dangerous reagents such as sodium azide, and high-pressure equipment for hydrogenation reaction
This synthetic route may be extremely harmful to the human body or the environment, and it is difficult to carry out industrial production and application

Method used

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  • Synthetic method of nitrogen-containing heterocyclic ferrocene derivatives
  • Synthetic method of nitrogen-containing heterocyclic ferrocene derivatives
  • Synthetic method of nitrogen-containing heterocyclic ferrocene derivatives

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preparation example Construction

[0031] The embodiments of the present invention provide a synthetic method of nitrogen-containing heterocyclic ferrocene derivatives, the reaction scheme of the synthetic method includes:

[0032]

[0033] Wherein, R are independently selected from C1-C3 alkyl;

[0034] Described synthetic method comprises the steps:

[0035] (1) introducing an aldehyde group on the nitrogen-containing heterocycle in the chemical structure of the raw material a to obtain the intermediate b;

[0036] (II) Carrying out the hydroxylamination reaction of the aldehyde group in the chemical structure of the intermediate b to form a hydroxylamine group to obtain the intermediate c;

[0037] (III) Reducing the hydroxylamine group in the chemical structure of the intermediate c to obtain the nitrogen-containing heterocyclic ferrocene derivative 1.

[0038] In one specific embodiment, R is C1 alkyl (ie methyl). More specifically, the number of R is 4, all of which are C1 alkyl groups, and the abov...

Embodiment 1

[0056] A synthetic method of a nitrogen-containing heterocyclic ferrocene derivative in this embodiment, the reaction scheme is as follows:

[0057]

[0058] The steps of the synthetic method are as follows:

[0059] (I) Synthesis of intermediate b

[0060] Add 400mg of raw material a (purchased from Aladdin, 1.5mmol), 7mL DMF (0.09mmol) into the reaction flask, lower the temperature of the system to 0°C, add 2mL of n-butyllithium solution (1.6M, 3.2mmol) dropwise, drop During the addition process, the temperature of the system is controlled at 0-5°C. After the dropwise addition, the temperature of the system is raised to 20-25°C to react for 1 hour; after the reaction is completed, add water to quench the reaction, extract with ethyl acetate, and distill the organic phase under reduced pressure to obtain intermediate Body b, dark red liquid 0.55g, purity 97%. 1H-NMR (300MHz, C 6 D. 6 )δ=10.15(s,1H), 5.04(s,1H), 4.68(s,1H), 4.04(s,1H), 1.64(s,15H), see the spectrum fig...

Embodiment 2

[0066] A synthetic method of a nitrogen-containing heterocyclic ferrocene derivative in this embodiment, its reaction scheme and steps are the same as in Example 1, the difference is that in step (1), n-butyllithium and N-methylmorpholine are used to introduce The formaldehyde.

[0067] Specifically, the steps of the synthesis method are as follows:

[0068] (I) Synthesis of intermediate b

[0069] Add 400 mg of raw material a (purchased from Aladdin, 1.5 mmol), 7 mL of N-methylmorpholine (0.06 mmol) into the reaction flask, lower the temperature of the system to 0 ° C, and dropwise add 2 mL of n-butyllithium solution (1.6 M, 3.2mmol), the temperature of the system is controlled at 0-5°C during the dropwise addition, and after the dropwise addition, the system is heated to 20-25°C for 1 hour; after the reaction is completed, quench the reaction by adding water, extract with ethyl acetate, and subtract the organic phase Pressure distillation gave 0.5 g of dark red liquid with...

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Abstract

The invention relates to a synthesis method of a nitrogen-containing heterocycles ferrocene derivative. The synthesis method comprises the following steps of (I) introducing an aldehyde group into nitrogen-containing heterocycles in the chemical structure of a raw material a to obtain an intermediate b; (II) performing a hydroxylamine reaction on the aldehyde group in the chemical architecture ofan intermediate b to obtain a hydroxylamine group namely an intermediate c; and (III), performing a reduction reaction on the hydroxylamine group in the chemical architecture of the intermediate c, toobtain the nitrogen-containing heterocycles ferrocene derivative 1. The synthesis method is simple in steps, reagents and equipment which have risks for human bodies or environment do not need to beadopted, and mass production and application of the nitrogen-containing heterocycles ferrocene derivative are convenient.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of nitrogen-containing heterocyclic ferrocene derivatives. Background technique [0002] Nitrogen-containing heterocyclic ferrocene derivatives have good fat solubility, can pass through the cell membrane smoothly, and interact with various enzymes, DNA, RNA and other substances in the cell. At the same time, the unique structure of the ferrocene group makes the nitrogen-containing heterocyclic ferrocene derivatives have a certain selective distribution, and the central iron ion can switch between +2 and +3 valences, making it have excellent redox reversibility. Easy to participate in biological metabolic process. Therefore, it is of great significance to study the synthesis of nitrogen-containing heterocyclic ferrocene derivatives. [0003] In the existing synthetic methods of ferrocene derivatives, ferrocene is mostly used as the core structure, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 徐亮蔡祥蒙发明李增李苏泳李彦雄郭俊毛波罗凤玲丸罔啓二
Owner FOSHAN ENANTIOSIC CORP LTD
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