Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Indazole derivatives and their applications

A technology for indazoles and derivatives is applied in the field of light-induced organic azide preparation of indazole derivatives, and achieves the effects of high yield, mild conditions and good inhibitory activity

Active Publication Date: 2022-04-22
CHINA THREE GORGES UNIV
View PDF0 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Indazole derivatives and their applications
  • Indazole derivatives and their applications
  • Indazole derivatives and their applications

Examples

Experimental program
Comparison scheme
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,...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses an indazole derivative and application thereof. Prepare o-azide benzaldehyde by the reaction of o-nitrobenzaldehyde and sodium azide; prepare intermediate azide from o-azidobenzaldehyde, amine compound, isonitrile compound; add intermediate azide in the Schlenk tube, Photo-induced Naichun insertion, aromatic ring isomerization and dehydrogenation reactions, after treatment, extraction with water and ethyl acetate, organic phase column chromatography separation to obtain indazole derivatives. This reaction can obtain higher yields of the target compound under sunlight. The application of the present invention is that the compound can be selectively used as a fungicide, and can be mixed with other plant protection-approved carriers or diluents, thereby being formulated into various commonly used dosage forms, such as mixtures, granules, water emulsions, etc., for use. It can also be used selectively or in combination with other pesticides such as insecticides, herbicides and plant growth regulators. In addition, molecules containing indazole skeletons 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com