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

Mechanical ball milling assisted synthesis method of 2-amino-3-cyano-4H-pyran compound

A technology of mechanical ball milling and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of heating synthesis time, tedious catalyst preparation, etc., achieve short reaction time, realize green synthesis, and wide application range

Pending Publication Date: 2021-11-09
ZHEJIANG UNIV OF TECH
View PDF11 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention provides a kind of 2-amino-3-cyano-4H-pyran compounds in the prior art in order to overcome the problems of cumbersome catalyst preparation, heating and long synthesis time in the synthesis process, in order to overcome the chemical synthesis of 2-amino-3-cyano-4H-pyran compounds in the prior art. -A mechanical milling-assisted synthesis method of amino-3-cyano-4H-pyran compounds, the synthesis reaction of this method is a solvent-free reaction, the reaction conditions are mild, the synthesis efficiency and yield are high, and the reaction uses protein as a catalyst, which has the advantages of Less pollution, friendly to the environment, etc.

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
  • Mechanical ball milling assisted synthesis method of 2-amino-3-cyano-4H-pyran compound
  • Mechanical ball milling assisted synthesis method of 2-amino-3-cyano-4H-pyran compound
  • Mechanical ball milling assisted synthesis method of 2-amino-3-cyano-4H-pyran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (a) Three stainless steel balls with a diameter of 10 mm were added to a 50 mL stainless steel ball mill jar, and then 0.5 mmol of benzaldehyde, 0.5 mmol of malononitrile, 0.5 mmol of dimedone, 50 mg of bovine serum albumin and 300 mg of Sodium chloride, ball milled for 30 minutes at 20Hz;

[0035] (b) After ball milling, scrape off the reaction mixture, add 30 mL of ethyl acetate to dissolve and filter, take the filtrate to concentrate by rotary evaporation, and finally purify by column chromatography, the eluent used is a mixed solution of petroleum ether and ethyl acetate , the volume ratio of sherwood oil and ethyl acetate is 4:1;

[0036] (c) The eluate containing the product was rotary evaporated to obtain 2-amino-3-cyano-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6, 7,8-tetrahydrobenzo[b]pyran, yield 72.8%.

[0037] The H NMR and C NMR spectra of the product are as follows: figure 2 As shown, its characterization data is m. p. 222-223 ℃, 1 HNMR (400 MHz, DMSO- d 6 )...

Embodiment 2

[0039](a) Three stainless steel balls with a diameter of 10 mm were added to a 50 mL stainless steel ball mill jar, and then 0.5 mmol of benzaldehyde, 0.5 mmol of malononitrile, 0.5 mmol of dimedone, 50 mg of bovine serum albumin and 300 mg of Sodium chloride, ball milled for 40 minutes at 30Hz;

[0040] (b) After ball milling, scrape off the reaction mixture, add 30 mL of ethyl acetate to dissolve and filter, take the filtrate to concentrate by rotary evaporation, and finally purify by column chromatography, the eluent used is a mixed solution of petroleum ether and ethyl acetate , the volume ratio of sherwood oil and ethyl acetate is 4:1;

[0041] (c) The eluate containing the product was rotary evaporated to obtain 2-amino-3-cyano-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6, 7,8-Tetrahydrobenzo[b]pyran, the yield was 96.0%.

[0042] The characterization data of this product are the same as the product of Example 1.

Embodiment 3

[0044] (a) Three stainless steel balls with a diameter of 10 mm were added to a 50 mL stainless steel ball mill jar, followed by 0.5 mmol benzaldehyde, 0.5 mmol malononitrile, 0.5 mmol dimedone and 50 mg bovine serum albumin, 30 Hz Ball milling for 30 minutes;

[0045] (b) After ball milling, scrape off the reaction mixture, add 30 mL of ethyl acetate to dissolve and filter, take the filtrate to concentrate by rotary evaporation, and finally purify by column chromatography, the eluent used is a mixed solution of petroleum ether and ethyl acetate , the volume ratio of sherwood oil and ethyl acetate is 4:1;

[0046] (c) The eluate containing the product was rotary evaporated to obtain 2-amino-3-cyano-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6, 7,8-Tetrahydrobenzo[b]pyran in 42.5% yield.

[0047] The characterization data of this product are the same as the product of Example 1.

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 relates to the technical field of chemical synthesis, and discloses a mechanical ball milling assisted synthesis method of a 2-amino-3-cyano-4H-pyran compound in order to solve the problems that in the prior art, a chemical method for synthesizing a 2-amino-3-cyano-4H-pyran compound cause large pollution and uses a catalyst which is tedious in preparation. The method comprises the following steps: (a) by taking a substrate 1, a substrate 2 and malononitrile as raw materials, adding a protein catalyst and a grinding aid, and then carrying out mechanical ball milling; and (b) after the ball milling is finished, scraping out a reactant, adding a solvent, filtering, concentrating, and carrying out column chromatography to obtain the 2-amino-3-cyano-4H-pyran compound. The mechanical ball milling technology is beneficial to mutual contact of reactant molecules, solvent-free reaction is achieved, and the protein catalyst is easy to obtain and environmentally friendly. Green synthesis of the 2-amino-3-cyano-4H-pyran compound is effectively realized, the preparation condition is mild, the operation is simple and convenient, and the reaction rate is high.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a mechanical ball milling-assisted synthesis method of 2-amino-3-cyano-4H-pyran compounds. Background technique [0002] 2-Amino-3-cyano-4H-pyran compounds have a variety of important biological and pharmacological activities, such as anti-tumor, anti-bacterial, anti-allergic and anti-aging functions. Such compounds are generally prepared by chemical methods, but chemical methods have disadvantages such as complex catalyst preparation and difficult product separation, which restrict the practical application of chemical synthesis of 2-amino-3-cyano-4H-pyran compounds, and Commonly used chemical synthesis requires the use of organic reagents as solvents, which will cause greater pressure on the environment. [0003] For example, a "supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4H-pyran compounds" disclosed in Chinese patent liter...

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): C07D311/58C07D407/04C07D409/04
CPCC07D311/58C07D407/04C07D409/04
Inventor 姜灵鲁青青储消和
Owner ZHEJIANG UNIV OF TECH
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