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Synthesis method and application of 2-aminonaphtho [2, 1-d] thiazole compound promoted by visible light

A synthesis method and technology of aminonaphthalene, applied in the direction of organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of high reaction temperature, few synthesis methods, inapplicability of aliphatic primary amines and aryl amines, etc., and achieve the preparation process And the effects of simple device, improved reaction yield and mild reaction conditions

Active Publication Date: 2020-08-21
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, literature research shows that there are few synthetic methods for such compounds, and all of them have some disadvantages, such as difficult and easy preparation of substrate sources, high reaction temperature, and the need to use metal catalysts, etc.
This limits the large-scale synthesis and application of such compounds to a certain extent, and cannot meet the screening requirements of active lead compounds in the development of new drugs.
In 2017, Professor Lei Aiwen's research group at Wuhan University developed a new method for the electrocatalytic synthesis of benzothiazole compounds (Green Chem., 2017, 19, 2092), but aliphatic primary amines and aryl amines cannot apply to the method
In the same year, the research group of Professor Fan Xuesen of Henan Normal University reported the method of iodine-catalyzed synthesis of 2-aminobenzothiazole (J.Org.Chem., 2017, 82, 9637), but the reaction used chlorobenzene which is more toxic As a solvent, and the reaction temperature is higher

Method used

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  • Synthesis method and application of 2-aminonaphtho [2, 1-d] thiazole compound promoted by visible light
  • Synthesis method and application of 2-aminonaphtho [2, 1-d] thiazole compound promoted by visible light
  • Synthesis method and application of 2-aminonaphtho [2, 1-d] thiazole compound promoted by visible light

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Effect test

Embodiment 1

[0055] A visible light-promoted synthesis method of 2-aminonaphtho[2,1-d]thiazole compounds, using substituted 2-naphthyl isothiocyanate and substituted organic amines as raw materials, and using a photosensitizer as a photocatalyst, Under the condition of organic solvent and oxygen, 2-aminonaphtho[2,1-d]thiazole compounds are synthesized by irradiating the reaction solution with a blue LED lamp as the light source;

[0056] Wherein, the general formula of the 2-aminonaphtho[2,1-d]thiazole compound is shown in formula I; the general formula of the substituted 2-naphthyl isothiocyanate is shown in formula II; The general formula of the substituted organic amine is shown in formula III;

[0057]

[0058] In the formula:

[0059] R 1 A substituent connected to the aromatic ring, selected from one of halogen and methoxy substituents;

[0060] R 2 and R 3 Both are alkyl groups, or one of them is an alkyl group and the other is an aromatic ring, or one of them is a hydrogen ...

Embodiment 2

[0068] A kind of synthetic method that visible light promotes 2-aminonaphtho[2,1-d]thiazole compound, reaction formula is as follows Figure 4 as shown,

[0069] At room temperature, add successively the isothiocyanate-2-naphthyl ester (0.2mmol) in the above reaction formula and the organic amine (0.3mmol ), alcohol-soluble eosin (0.002mmol), and 2.0mL DMSO was added with a syringe under oxygen conditions, and the reaction tube was placed 3 cm away from a 12-watt blue LED lamp, and irradiated and stirred for 24 hours. After the reaction is over, add 2 mL of deionized water to the reaction solution, mix well, use 3 mL of ethyl acetate as the extractant each time to extract the crude product from the reaction solution, combine the extracts, and rotate The solvent was removed by the evaporator; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (5:1v / v)) to obtain 49 mg of ...

Embodiment 3

[0077] A kind of synthetic method that visible light promotes 2-aminonaphtho[2,1-d]thiazole compound, reaction formula is as follows Figure 5 Shown:

[0078] At room temperature, add successively the isothiocyanate-2-naphthyl ester (0.2mmol) in the above reaction formula and the organic amine (0.3mmol ), alcohol-soluble eosin (0.002mmol), and 2.0mL DMF was added with a syringe under oxygen conditions, and the reaction tube was placed 3 cm away from a 12-watt blue LED lamp, and irradiated and stirred for 24 hours. After the reaction is over, add 2 mL of deionized water to the reaction solution, mix well, use 3 mL of ethyl acetate as the extractant each time to extract the crude product from the reaction solution, combine the extracts, and rotate The solvent was removed by the evaporator; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (15:1v / v)) to obtain 44 mg of the...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a synthesis method and application of a 2-aminonaphtho [2, 1-d] thiazole compound promoted by visible light. Substituted isothiocyanate-2-naphthyl ester and substituted organic amine are used as raw materials, an organic dye is used as a photocatalyst, and under the conditions of an organic solvent and oxygen, a reaction solution is irradiated with near blue light to synthesize the 2-aminonaphtho [2, 1-d] thiazole compound. The synthesis method provided by the invention is suitable for synthesizing and screening anticancer or antiviral biological medicine lead compounds. The synthesis method provided by the invention is simple in preparation process and device, harsh synthesis conditions are not needed, thereaction can be completed in one step, and the synthesis method is suitable for synthesizing various 2-aminonaphtho [2, 1-d] thiazole compounds and derivatives, has relatively high universality to various functional groups on aromatic rings, and has no special limitation on the 2-aminonaphtho [2, 1-d] thiazole compound and the number and types of substituents of organic amine.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method and application of visible light-promoted 2-aminonaphtho[2,1-d]thiazole compounds. Background technique [0002] Thiazoles are a class of aromatic five-membered heterocyclic compounds containing nitrogen and sulfur atoms, and have shown great application value in the fields of medicine, pesticides, and materials. The application and development of thiazole compounds has aroused widespread interest and has become one of the hot research areas in recent years. As one of the important derivatives of thiazole, 2-aminonaphtho[2,1-d]thiazole compounds have also attracted the attention of chemists for their synthesis methods and applications. However, literature research shows that there are few synthetic methods for this type of compound, and all of them have some disadvantages, such as difficult and easy preparation of substrate sources, high reaction tem...

Claims

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Application Information

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IPC IPC(8): C07D277/84C07D417/12C07D487/04A61P35/00A61P31/12
CPCC07D277/84C07D417/12C07D487/04A61P35/00A61P31/12
Inventor 杨道山甘子玉颜秋莉
Owner QINGDAO UNIV OF SCI & TECH