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Method for synthesizing benzoxanthene derivatives

A technology for benzoxanthene and derivatives, which is applied in the field of synthesizing benzoxanthene derivatives, can solve the problems of complicated operation process, serious equipment corrosion, high catalyst cost, etc., and achieves wide sources of raw materials, reduced production costs, and post-processing Easy to handle effects

Inactive Publication Date: 2015-04-15
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] These methods of above-mentioned report have following one or more shortcomings: the cost of catalyst is higher; the preparation process of catalyst is complicated; the catalyst cannot be recycled; the equipment is seriously corroded; operation, does not have large-scale industrial applications, etc.

Method used

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  • Method for synthesizing benzoxanthene derivatives
  • Method for synthesizing benzoxanthene derivatives
  • Method for synthesizing benzoxanthene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 25mL round-bottomed flask, add 10mmol (1.061g) benzaldehyde, 10mmol (1.121g) 1,3-cyclohexanedione, 10mmol (1.442g) β-naphthol, 4mL glycerol in sequence, and place at 95°C under normal pressure Mix and stir for 2.5 hours, cool, add 10 mL of water, and let stand overnight. Filter and wash with cold water, and recrystallize from 95% ethanol to obtain pure 12-phenyl-benzoxa[a]anthracene with a yield of 87%.

Embodiment 2

[0024] In a 25mL round bottom flask, add 10mmol (1.061g) benzaldehyde, 10mmol (1.402g) 5,5-dimethyl-1,3-cyclohexanedione, 10mmol (1.442g) β-naphthol, 5mL Glycerin, mixed and stirred at 92°C under normal pressure for 2.0 hours, cooled, added 10 mL of water, and stood overnight. Filter and wash with cold water, and recrystallize from 95% ethanol to obtain pure 9,9-dimethyl-12-phenyl-benzoxa[a]anthracene with a yield of 89%.

Embodiment 3

[0026] In a 25mL round bottom flask, add 10mmol (1.221g) 4-hydroxybenzaldehyde, 10mmol (1.402g) 5,5-dimethyl-1,3-cyclohexanedione, 10mmol (1.442g) β-naphthalene Phenol, 15mL glycerin, mixed and stirred at 90°C under normal pressure and refluxed for 1.5 hours, cooled, added 20mL of water, and stood overnight. Filter and wash with cold water, and recrystallize from 95% ethanol to obtain pure 9,9-dimethyl-12-(4-hydroxy-phenyl)benzoxa[a]anthracene with a yield of 83%.

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Abstract

The invention discloses a novel method for synthesizing benzoxanthene derivatives. The method comprises the following step: by taking beta-naphthol, aromatic aldehyde and 1,3-cyclohexanedione derivatives as raw materials and glycerol as a reaction medium, performing heating reaction at normal pressure without using any catalyst, thus obtaining the benzoxanthene derivatives. Compared with the prior art, the method disclosed by the invention has the following advantages: (1) the glycerol is used as the reaction medium, and the raw materials are wide in sources, thereby ensuring that the method is green and environment-friendly; (2) no catalyst is needed, the process is convenient, and the aftertreatment is convenient; and (3) no other organic solvent is used, thereby achieving dual environmental and economic benefits. The process disclosed by the invention is an efficient environment-friendly method for synthesizing benzoxanthene derivatives, and is beneficial to large-scale industrial production.

Description

a technical field [0001] The invention relates to a new method for synthesizing benzoxanthene derivatives, belonging to the technical field of chemical material preparation. The method is suitable for the occasion of synthesizing benzoxanthene derivatives by using β-naphthol, aromatic aldehyde and 1,3-cyclohexanedione derivatives as raw materials. Two background technology [0002] The skeleton structure of anthracene in benzoxanthene compounds widely exists in many natural compounds with biological activity, and different structures exhibit different properties, and different spatial structures exhibit different biological activities. Benzoxanthene is an intermediate in the synthesis of various drugs, and it has been found to have antitumor, antiviral, antibacterial, anti-inflammatory and anti-implantation activities; in addition, benzoxanthene is used as a photosensitizing dye in laser technology It has important application value. [0003] Based on the unique physiologi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/78
CPCC07D311/78
Inventor 方东邢胜先王岩吉海峰宋云王慧
Owner YANCHENG TEACHERS UNIV