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

1,2,3-Triazole derivative as well as synthesis and application thereof

A technology of triazole derivatives and trifluoromethyl, which is applied in the field of 1,2,3-triazole derivatives and their synthesis, achieves the effects of high yield of reaction products, mild synthesis reaction conditions, and simple reaction operation

Active Publication Date: 2019-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of 1,2,3-triazole compounds by cyclization of S,N-substituted internal alkenes with aryl diazonium salts has not been reported yet.

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
  • 1,2,3-Triazole derivative as well as synthesis and application thereof
  • 1,2,3-Triazole derivative as well as synthesis and application thereof
  • 1,2,3-Triazole derivative as well as synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] To the 25mL branch tube, add CuBr in sequence 2 (0.09mmol), K 3 PO 4 (0.15mmol), K 2 S 2 o 8 (1.0mmol), S,N-substituted internal olefin 2a (0.3mmol), diazonium salt 3a (0.6mmol), CH 3 CN 3mL, O 2 The reaction was carried out at 25° C. for 5 hours under an atmosphere. After the reaction was over, the solvent was removed under reduced pressure, separated by silica gel column chromatography (the eluent was petroleum ether (60-90° C.) / ethyl acetate, v / v=20:1), and the target product 1a (82 mg , yield 88%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0035]

[0036] The reaction steps and operation are the same as in Example 1, and the difference from Example 1 is that the catalyst is copper chloride. The reaction was stopped, and the target product 1a (72 mg, yield 77%) was obtained after post-treatment.

Embodiment 3

[0038]

[0039] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is that alkali is K 2 CO 3 . The reaction was stopped, and the target product 1a (65 mg, yield 70%) was obtained after post-processing.

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 1,2,3-triazole derivative and a synthesis method thereof. S,N-Substituted internal olefin and aryl diazonium salt are used as initial raw materials, copper salt is used as acatalyst, and cyclization is performed in the presence of alkali and an oxidizing agent in an organic solvent to obtain 1,2,3-triazole derivative. By designing the substrate configuration, 1,2,3-triazole derivative with potential biological activity is simply and conveniently synthesized. The method has the advantages of accessible raw materials, wide substrate range, mild synthesis reaction conditions and high reaction product yield, is simple to operate, and has diversified functional groups.

Description

technical field [0001] The invention belongs to the technical field of chemical organic synthesis, and relates to a 1,2,3-triazole derivative and a synthesis method thereof. technical background [0002] 1,2,3-triazole compounds are an important class of heterocyclic compounds. Due to their unique chemical properties and biological activities, they have been widely used in many fields such as medicine, materials and biology. In medicinal chemistry, they have 1 , Compounds with 2,3-triazole skeleton structure exhibit various biological activities such as anti-virus, anti-cancer, anti-bacteria and anti-tuberculosis. At present, there are mainly three methods for the synthesis of 1,2,3-triazole compounds: 1) Transition metal-catalyzed 1,3-dipolar cycloaddition reaction of organic azides and alkynes (Angew. Chem. Int. Ed.2002,41,2596); 2) 1,3-dipolar cycloaddition reaction of organic azides and ketones catalyzed by small organic molecules (Angew.Chem.Int.Ed.2014,53,10420);3 ) ...

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): C07D249/06C07D487/04
Inventor 余正坤吴苹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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