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

A kind of 3-aryl indoxazine acetate derivative and its preparation method and application

A technology of aryl indoleazine acetate and indoleazine acetate, which is applied in the field of 3-aryl indoleazine acetate derivatives and their preparation, and can solve difficult aryl chloride bonds and poor chemical reactivity and other problems, to achieve the effect of mild reaction conditions, good reaction effect, and stable and easy-to-obtain reaction reagents

Inactive Publication Date: 2017-12-12
SHAOXING UNIVERSITY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Under palladium-catalyzed conditions, the use of aryl chlorides as substrates is relatively more challenging due to their poor chemical reactivity and the difficulty of oxidizing aryl chloride bonds with palladium.

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
  • A kind of 3-aryl indoxazine acetate derivative and its preparation method and application
  • A kind of 3-aryl indoxazine acetate derivative and its preparation method and application
  • A kind of 3-aryl indoxazine acetate derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] (1) Preparation of indolezine: first slowly add bromoacetic acid (50mmol) to a solution of pyridine (50mmol) in ethyl acetate (30mL), stir the mixture at room temperature for 3 hours, filter and dry to obtain white solid N-(carboxymethyl base) pyridinium bromide. N-(carboxymethyl)bromopyridinium salt (10mmol, 2.04g), vinyl acetate (30mmol), triethylamine (1.5mL), active manganese dioxide (80mmol) were reacted in toluene (80mL) at 90°C for 2 hours , TLC detects the reaction, after the reaction is completed, the solid is filtered off and washed with acetone, the combined organic phase is spin-dried, and the mixture is separated by column to obtain indolezine acetate.

[0040] (2) Indoleazine arylation reaction: Indoleazine acetate (0.3mmol), sodium aryl sulfinate (0.6mmol), catalyst (0.03mmol), ligand (0.05mmol), oxidant (0.3mmol) Mix in acetonitrile (2mL), react at 100°C for 6h under nitrogen protection, after TLC detects that the reaction is complete, cool to room temp...

Embodiment 1～20

[0043] The catalysts of Examples 1-20 were palladium acetate, without adding ligands, and reacted with different oxidants. The reaction results are shown in Table 1.

[0044] The reaction conditions and the result of table 1 embodiment 1~20

[0045] Example

Embodiment 21～37

[0047] The oxidant of Examples 21-37 was tert-butyl peroxyacetate, and the catalyst and ligand were changed. The results obtained are shown in Table 2.

[0048] The reaction conditions and the result of table 2 embodiment 21~37

[0049] Example

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 a 3-aryl indolezine acetate derivative and its preparation method and application. The preparation method comprises the following steps: under the action of a divalent palladium catalyst, a nitrogen-containing ligand and a peroxide, The desulfurization arylation reaction of indoleazine acetate and sodium aryl sulfinate occurs, and after the reaction is complete, the 3-aryl indole azine acetate derivative is obtained through post-processing. The preparation method effectively promotes the reaction by adding a specific peroxide additive in the reaction system, inhibits the self-coupling reaction of aryl sulfonyl hydrazide, and improves the yield of the reaction; at the same time, the reaction reagent used is stable It is easy to obtain and is convenient for mass production, which provides a new and effective way to construct this type of structure; in addition, the results of activity tests show that the product can inhibit cell proliferation to a certain extent and has certain antitumor activity. Therefore, the preparation The method and the product thereof have important application significance in the field of medicine.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a 3-aryl indolezine acetate derivative and a preparation method and application thereof. Background technique [0002] Today, indoxazines have become an important class of nitrogen-containing heterocyclic structures, which are commonly found in the fields of natural product synthesis and medicine. Indolezines derivatives exhibit antibacterial activity, estrogen receptor binding activity, antituberculous activity, phosphatase inhibitory activity and anticancer activity. and have been obtained as antidiabetic, anti-inflammatory, antihistamine and antiacetylcholine agents, antioxidants, phosphodiesterase inhibitors, PDE5A inhibitors, L-type calcium channel blockers and synthesis inhibitors of leukotrienes It has been widely used (V. Sharma and V. Kumar, Med. Chem. Res. 2014, 23, 3593.). [0003] Therefore, a number of methods for the synthesis of functionalized indoleaz...

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): C07D471/04A61P35/00
CPCC07D471/04
Inventor 朱余玲赵保丽
Owner SHAOXING UNIVERSITY
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