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

Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin

A technology of 1H-1 and triazole, which is applied in the field of organic and pharmaceutical synthesis, can solve problems such as limiting the scope of application, and achieve the effects of simple operation, effective synthesis method, and economical raw materials

Inactive Publication Date: 2011-07-20
TONGJI UNIV
View PDF4 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few synthetic methods reported in the literature, thus limiting the scope of its application.

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
  • Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin
  • Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin
  • Method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of 4-p-tolyl-1 hydrogen-1,2,3-triazole

[0025]

[0026] Add cuprous iodide (0.04 mmol), sodium ascorbate (0.1 mmol), sodium azide (0.4 mmol), potassium carbonate (0.4 mmol), p-cresyl dibromide (0.2 mmol), and dimethyl Sulfoxide 2.5mL at 100 o C under magnetic stirring reaction for 16 hours, after the completion of the reaction, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The volume ratio of ether=3:1 was the eluent, and the desired product was purified by column chromatography to obtain the desired product as a tan solid with a yield of 83%.

[0027] Its NMR data are as follows:

[0028] 1 H NMR (500 MHz, CDCl 3 ): δ = 2.39(s, 3 H), 7.26 (d, J = 7.0 Hz, 2 H), 7.71 (d, J = 8.0 Hz, 2 H), 7.94 (br s, 1 H).

Embodiment 2

[0029] Example 2: Synthesis of 4-p-cumyl-1 hydrogen-1,2,3-triazole

[0030]

[0031] Add cuprous iodide (0.04 mmol), sodium ascorbate (0.1 mmol), sodium azide (0.4 mmol), cesium carbonate (0.4 mmol), p-cresyl dibromide (0.2 mmol), and dimethyl Sulfoxide 2.5mL at 100 o C under magnetic stirring reaction for 16 hours, after the completion of the reaction, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The volume ratio of ether=3:1 was used as the eluent and purified by column chromatography to obtain the desired product as a light yellow solid with a yield of 79%.

[0032] Its NMR data are as follows:

[0033] 1 H NMR (500 MHz, CDCl3 ): δ = 1.27-1.29( d , J=6.95 Hz ,6H ), 2.94-2.96 ( m, 1H ), 7.31-7.33 (d , J=8.0 Hz,2H ), 7.73- 7.75 (d, J= 8.3Hz, 2H), 7.94 (br s, 1H).

Embodiment 3

[0034] Example 3: Synthesis of 4-p-bromophenyl-1 hydrogen-1,2,3-triazole

[0035]

[0036] Add cuprous bromide (0.04 mmol), sodium ascorbate (0.1 mmol), sodium azide (0.4 mmol), DBU (0.4 mmol), p-bromostyryl dibromide (0.2 mmol), and dimethyl Sulfoxide 2.5mL at 100 o C under magnetic stirring reaction for 10 hours, after the reaction was completed, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The volume ratio of ether=3:1 is the eluent and purified by column chromatography to obtain the desired product as a light yellow solid with a yield of 65%.

[0037] Its NMR data are as follows:

[0038] 1 H NMR (500 MHz, CDCl 3 ): δ = 7.57-7.60 (d, J= 8.5 Hz, 2H), 7.69-7.71 (d, J= 8.5 Hz, 2H), 7.95(br s, 1H).

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 technical fields of medicaments and organic synthetic intermediates and in particular relates to a method for synthesizing 4-aryl-1H-1,2,3-triazole by using 1,1-dibromo-1-olefin. A 4-aryl-1,2,3-triazole compound is synthesized by using a sodium azide or organic nitrine compound and cheap and readily-available 1,1-dibromo-1-olefin as raw materials in the presence of alkali in dimethylsulfoxide through copper catalysis conveniently. The compound comprises a 1,2,3-triazole structure unit with bioactivity and can be used for synthesizing and modifying the organic synthetic intermediates and the medicaments. A novel and effective synthetic method is provided for medicament screening.

Description

technical field [0001] The invention belongs to the technical field of organic and pharmaceutical synthesis, and specifically relates to the synthesis of 4-aryl-1 by using a 1,1-dibromo-1-alkene H - 1,2,3-triazole method. Background technique [0002] Triazole heterocyclic compounds have a wide range of biological activities and have broad application prospects in the fields of medicine, agriculture and materials, and have always been valued by medicinal chemists and biochemists. Among them, 1,2,3-triazole compounds have been gradually developed in recent years, and have significant effects on antibacterial, bactericidal, immune, treatment of tumors, arthritis, rickets, neurotic disorders, etc. (Michael J. G , et al. J. Med. Chem., 2000, 43 , 953-970). [0003] 1,2,3-triazole compounds are an important class of heterocyclic compounds (Alvarez R, et al. J. Med. Chem. , 1994, 37 , 4185-4194), the five-membered heterocyclic ring in the compound has lower toxicity than im...

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): C07D249/06
Inventor 匡春香王晓昆
Owner TONGJI 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