Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for catalytic oxidization synthesis of anthone compound

A technology of catalytic oxidation and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of separation of product and N-hydroxyphthalimide, expensive ligands, etc., achieves low cost, reduced environmental cost, simple and safe operation Effect

Active Publication Date: 2017-06-30
ZHEJIANG UNIV OF TECH
View PDF0 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some researchers reported that Fe(NO 3 ) 3 9H 2 O and N-hydroxyphthalimide are combined catalysts, and oxygen is used to oxidize xanthene to xanthone, but due to the use of more N-hydroxyphthalimide, it will cause Separation of product and N-hydroxyphthalimide ( Catal. Sci. Technol. 2016, 6 , 1378)
Other researchers have reported iron complex-catalyzed, visible-light-driven oxygen oxidation of xanthenes and thioxanthenes, which is also flawed because the ligands used are very expensive ( Angew. Chem. Int. Ed. 2016, 55 , 427)

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 catalytic oxidization synthesis of anthone compound
  • Method for catalytic oxidization synthesis of anthone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of Xanthone (Formula (2-1))

[0028] Into a 35mL sealed tube, add 1mmol of xanthene (formula (1-1)), 0.1mmol of Fe(NO 3 ) 3 9H 2 O, 0.2 mmol of KPF 6 and 3mL of acetonitrile, replace the air in the tube with oxygen, seal the mouth of the bottle with a rubber stopper, insert an oxygen bulb, put the reaction bottle into a preheated oil bath and heat it to 80°C, and react for 2h. Filtrate, distill the filtrate to remove the solvent under reduced pressure, and then conduct column chromatography separation, use ethyl acetate / petroleum ether with a volume ratio of 1:50 as the eluent, collect the eluate containing the target compound, and evaporate the solvent to obtain The product xanthone has an isolated yield of 95%.

Embodiment 2

[0029] Example 2: Preparation of Xanthone (Formula (2-1))

[0030] Reaction steps are with embodiment 1, difference is that KPF 6 Change to NaBF 4 , The isolated yield of xanthene was 91%.

Embodiment 3

[0031] Example 3: Preparation of Xanthone (Formula (2-1))

[0032] The reaction steps are the same as in Example 1, except that the reaction temperature is changed to 85° C., and the isolated yield of xanthene is 95%.

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 method for catalytic oxidation synthesis of an anthone compound. The method is carried out according to the following steps: adding an anthene compound, Fe(NO3)3*9H2O and a fluorine-containing inorganic salt into an acetonitrile solvent, and performing a reaction for 2-12h at 75-85 DEG C under a normal pressure oxygen condition to obtain the anthone compound, wherein the mass ratio of the reaction substrate namely the anthone compound, Fe(NO3)3*9H2O and the fluorine-containing inorganic salt is 100:(8-15):(15-30), and after the completion of the reaction, the anthone compound can be obtained by adopting conventional column separation purification. The method provided by the invention is simple, convenient and safe to operate, and has the following beneficial effects: A) clean oxygen is used as an oxidant in the method, so that the environmental cost is greatly reduced; and B) Fe(NO3)3*9H2O is used as a catalyst in the method, so that the cost is low.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a catalytic oxidation synthesis method of xanthone compounds. Background technique [0002] Xanthone compounds include xanthone, azaxanthone and thioxanthone compounds, these structures exist in many biologically active natural products and synthetic drugs with important biological properties, and many xanthone derivatives Has certain pharmacological effects. [0003] Therefore, the research and development of synthetic methods for these compounds has attracted the attention of many people. In recent years, a number of synthetic routes for xanthone compounds have been developed. Among them, the most concise and convenient method is to obtain xanthone by one-step oxidation of xanthene as a raw material. Initially, people directly used Cr-based oxidants and Mn-based oxidants for one-step oxidation, but the stoichiometric use of such oxidants is obviously not ...

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): C07D311/82C07D311/78C07D335/12
CPCC07D311/78C07D311/82C07D335/12
Inventor 沈振陆李美超洪超胡信全莫卫民
Owner ZHEJIANG UNIV OF TECH