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

Aza fused ring compound and synthesis method thereof

A synthesis method and compound technology, applied in the direction of steroids, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of overall synthesis complexity, limited product range, etc., and achieve good functional group compatibility Sexual and efficient introduction of the effect

Pending Publication Date: 2022-08-02
NORTHWEST UNIV(CN)
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While this strategy works, the use of directing groups complicates the overall synthesis and limits the range of obtainable products

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
  • Aza fused ring compound and synthesis method thereof
  • Aza fused ring compound and synthesis method thereof
  • Aza fused ring compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] The invention provides a method for synthesizing aza-fused-ring compounds, which comprises the following steps: taking substituted or unsubstituted heteroaryl ketone and halide as raw materials, and dearomatizing in the presence of a palladium catalyst, a ligand and a solvent The reaction generates a spiro-ring intermediate, and the spiro-ring intermediate undergoes the intramolecular acyl migration driven by aromatization to induce the skeleton rearrangement of the heteroaryl ketone to obtain the compound represented by formula I or formula II:

[0040]

[0041] Wherein, X is selected from sulfur atom, nitrogen atom or oxygen atom;

[0042] R2, R3, R4, R5, R6, R7 are independently selected from alkyl, aryl, ester, sulfonyl, mercapto, amino, boryl, halogen, thioether, sulfinyl, phospholipid, alkene, alkyne group, selenide, fluorine-containing alkane or deuterated atom;

[0043] The synthetic route is as follows:

[0044]

[0045] The preparation of (benzo)imidaz...

Embodiment 1

[0068] Using (1-methyl-1H-benzo[d]imidazol-2-yl)(2-vinylphenyl)methanone 1 (0.1 mmol) as a model substrate, ethyl difluorobromoacetate (BrCF 2 COOEt) (0.15mmol, 1.5 equiv) as coupling agent, palladium dichloride (0.01mmol, 10mol%) as catalyst, 1,5-bis(diphenylphosphine)pentane (dpppent) (0.012mmol, 12mol%) ) as a ligand, and sodium carbonate (0.1 mmol, 1.0 equiv.) was added to react 24 in a mixed solvent of 1,4-dioxane and tetrahydrofuran (volume ratio 1:2) (1.0 mL) at a temperature of 130 °C. Within hours, product 1 was obtained in 90% yield.

[0069]

[0070] Yellow solid, Mp=253–254°C. 1H NMR (400MHz, CDCl 3 )δ=8.79–8.77 (m, 1H), 8.50–8.48 (m, 1H), 7.59–7.53 (m, 2H), 7.34–7.26 (m, 2H), 7.19–7.14 (m, 1H), 7.05– 7.02 (dd, J=1.2Hz, J=8.0Hz, 1H), 4.20–4.15 (m, 2H), 3.87–3.81 (m, 5H), 1.19–1.16 (m, 3H). 13C NMR (100MHz, CDCl) 3 )δ=164.36(t,J=32.0Hz), 159.59,140.87,138.07,135.08,132.04,127.57,127.50,125.70,122.43,121.36, 121.14,118.91,116.84,115.18,106.73,79.91,63.19,32.68,...

Embodiment 2

[0072] Using (1-methyl-1H-benzo[d]imidazol-2-yl)(2-vinylphenyl)methanone 1 (0.1 mmol) as a model substrate, ethyl difluorobromoacetate (BrCF 2 COOEt) (0.1 mmol, 1.0 equiv) as coupling agent, palladium acetate (0.01 mmol, 10 mol%) as catalyst, 1,5-bis(diphenylphosphine)pentane (dpppent) (0.012 mmol, 12 mol%) as catalyst ligand, and sodium carbonate (0.12 mmol, 1.2 equiv.) was added, and the mixed solvent of 1,4-dioxane and tetrahydrofuran (volume ratio 1:2) (1.0 mL) was reacted for 24 hours at a temperature of 130 °C, Product 1 was obtained in 54% yield.

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 belongs to the field of medicinal chemistry, and particularly discloses an aza fused ring compound and a synthesis method thereof. The compound is synthesized according to the following steps: taking substituted or unsubstituted heteroaryl ketone and halide as raw materials, carrying out a dearomatization reaction in the presence of a palladium catalyst, a ligand and a solvent to generate a spiro intermediate, initiating skeleton rearrangement of the heteroaryl ketone by the spiro intermediate through intramolecular acyl migration driven by aromatization, and obtaining the compound. And preparing a compound as shown in a formula I or a formula II. The synthesis method provided by the invention has good functional group compatibility, is suitable for skeleton rearrangement of imidazolone compounds, and also can be used for skeleton rearrangement of thiazole and oxazolone; the method can also be used for rapidly and efficiently introducing the aza fused ring structure in complex natural products and drug molecules.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically discloses an aza-fused ring compound and a synthesis method thereof. Background technique [0002] Condensed nitrogen heterocyclic compounds are important structural units in organic synthesis, medicine, pesticides, materials, etc. Aromatic aza-fused ring structures are common in natural products and pharmaceutical molecules. Aza-fused-ring compounds have good biological activity and are widely used in anti-tumor, treatment of insomnia and so on. Aza-fused ring compounds also have special fluorescence properties, and also have important applications in fluorescent probes, organic light-emitting materials and so on. Therefore, the synthesis of nitrogen heterocyclic compounds has attracted the attention of many organic chemists. From the perspective of the construction of heterocycles, the synthesis of such compounds is mainly through the construction of a single ring and the ...

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 Applications(China)
IPC IPC(8): C07D471/04C07J43/00C07F9/6561C07D513/04C07D498/04C07D519/00C07D235/26C07D235/12
CPCC07D471/04C07J43/003C07F9/6561C07D513/04C07D498/04C07D519/00C07D235/26C07D235/12Y02E10/549
Inventor 郑兆静魏颢
Owner NORTHWEST UNIV(CN)
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