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Indazole derivative and application thereof

A technology of derivatives and indazoles, applied in the field of light-induced organic azide preparation of indazole derivatives

Active Publication Date: 2021-09-10
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, visible light-driven N–N coupling of nitrides, directly enabling the synthesis of indazole compounds, has not been explored.

Method used

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  • Indazole derivative and application thereof
  • Indazole derivative and application thereof
  • Indazole derivative and application thereof

Examples

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Effect test

Embodiment 1

[0043] A method for preparing 2-(3-bromophenyl)-N-(tert-butyl)-2H-indazole-3-carboxamide, comprising the following experimental steps:

[0044] Weigh o-nitrobenzaldehyde (30mmol) into a 100mL round-bottomed flask, add HMPA solvent to fully dissolve, then add sodium azide (60mmol) to dissolve, and place it in a constant temperature oil bath at 60°C to start the reaction. After the reaction was monitored by TLC, the reaction solution was left to cool to normal temperature, and poured into an ice-water solution under uniform stirring and left to stand. It was observed that a light yellow solid was gradually precipitated. The post-treatment was simply filtered, washed and dried to obtain adjacent alkene Nitrobenzaldehyde. Take o-azidobenzaldehyde (1mmol, 1.0eqv.) and dissolve it in 2mL of methanol solvent, add equimolar 3-bromoaniline (1mmol, 1.0eqv.) and 0.2mmol of H 3 PO 4 After the reaction was carried out for 5 min, 1 mL of methanol was added for a complete reaction, and the...

Embodiment 2

[0048] A method for preparing N-(tert-butyl)-2-(4-methoxyphenyl)-2H-indazole-3-carboxamide, comprising the following experimental steps:

[0049] Weigh o-nitrobenzaldehyde (30mmol) into a 100mL round-bottomed flask, add HMPA solvent to fully dissolve, then add sodium azide (60mmol) to dissolve, and place it in a constant temperature oil bath at 60°C to start the reaction. After the reaction was monitored by TLC, the reaction solution was left to cool to normal temperature, and poured into an ice-water solution under uniform stirring and left to stand. It was observed that a light yellow solid was gradually precipitated. The post-treatment was simply filtered, washed and dried to obtain adjacent alkene Nitrobenzaldehyde. Take azidobenzaldehyde (1mmol, 1.0eqv.) and dissolve it in 2mL of methanol solvent, add equimolar 4-methoxyaniline (1mmol, 1.0eqv.) and 0.2mmol of H 3 PO 4 After the reaction was carried out for 5 min, 1 mL of methanol was added for a complete reaction, and t...

Embodiment 3

[0053] A method for preparing 2-(3-bromophenyl)-n-butyl-2H-indazole-3-carboxamide, comprising the following experimental steps:

[0054] Weigh o-nitrobenzaldehyde (30mmol) into a 100mL round-bottomed flask, add HMPA solvent to fully dissolve, then add sodium azide (60mmol) to dissolve, and place it in a constant temperature oil bath at 60°C to start the reaction. After the reaction was monitored by TLC, the reaction solution was left to cool to normal temperature, and poured into an ice-water solution under uniform stirring and left to stand. It was observed that a light yellow solid was gradually precipitated. The post-treatment was simply filtered, washed and dried to obtain adjacent alkene Nitrobenzaldehyde. Take o-azidebenzaldehyde (1mmol, 1.0eqv.) and dissolve it in 2mL of methanol solvent, add equimolar 4-methoxyaniline (1mmol, 1.0eqv) and 0.2mmol of H 3 PO 4 After the reaction was carried out for 5 minutes, 1 mL of methanol was added for a complete reaction, and then,...

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Abstract

The invention discloses an indazole derivative and application thereof. The method comprises the following steps of: reacting o-nitrobenzaldehyde with sodium azide to obtain o-azidobenzaldehyde; preparing an intermediate azide from the o-azidobenzaldehyde, an amine compound and an isonitrile compound; and adding the intermediate azide into a Schlenk tube, carrying out photoinduction to realize nitrene insertion, aromatic ring isomerization and dehydrogenation reaction, carrying out post-treatment, extracting with water and ethyl acetate, and carrying out organic phase column chromatography separation to obtain the indazole derivative. According to the reaction, a target compound with high yield can be obtained under sunlight. The compound can be selectively used as a bactericide, can be mixed with other carriers or diluents allowed by plant protection to obtain various common dosage forms, such as a mixture, granules and an emulsion in water, and can also be selectively mixed with other pesticides, such as an insecticide, a herbicide and a plant growth regulator for use or simultaneously used together with the pesticide, the herbicide and the plant growth regulator. In addition, the molecules containing the indazole skeleton have potential medicinal value.

Description

technical field [0001] The invention relates to a method for preparing indazole derivatives from light-induced organic azides and an application thereof, belonging to the technical field of organic synthesis. Background technique [0002] Organic photochemistry has a unique position in organic synthetic chemistry. It is a novel and green and efficient strategy to obtain a series of biologically and pharmaceutically active cyclic or heterocyclic compounds by using light-induced ring-closing reactions of complex molecules. Organic azides are important raw materials for organic reactions. It is of great significance and value to convert azides into nitrates by light or heat induction, and then obtain different types of nitrogen-containing heterocyclic compounds through further cyclization reactions. [0003] Indazole is a typical compound containing N-N bonds, and it is one of the most important heterocycles in medicinal chemistry. There are two main types of indazole derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/56A61P35/00A61P29/00A61P31/06A61P43/00A01N43/56A01P3/00
CPCC07D231/56A61P35/00A61P29/00A61P31/06A61P43/00A01N43/56
Inventor 王龙刘金妮刘娜王雅雯胡为民
Owner CHINA THREE GORGES UNIV
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