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Synthesis method of 9H-xanthene/ thioxanthene compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve problems such as difficult industrial production, unfavorable energy conservation and environmental protection, and achieve the effects of less waste discharge, high yield and simple reaction conditions

Active Publication Date: 2019-08-27
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention provides a synthesis of a 9H-oxygen / thioxanthene compound in order to overcome the defects of the above-mentioned prior art that are not conducive to energy conservation and environmental protection and are difficult to industrialized production The method provides a synthetic method that does not require metal catalysis, does not require peroxides, and does not require high-temperature reaction conditions. The reaction conditions are simple, the yield is high, and waste discharge is small, which is conducive to energy saving and environmental protection. The reaction equipment is simple and easy for industrial production.

Method used

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  • Synthesis method of 9H-xanthene/ thioxanthene compound
  • Synthesis method of 9H-xanthene/ thioxanthene compound
  • Synthesis method of 9H-xanthene/ thioxanthene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Synthetic method of 9-(2,4-dimethoxyphenyl)-9H-oxanthene.

[0047] Take a 15mL pressure-resistant reaction tube, add DDQ 45mg, xanthene 36mg, 1,3-dimethoxybenzene 83mg, molecular sieve 100mg, acetonitrile 2mL, open the reaction, and stir at room temperature for 12h. After the reaction, 10 mL of ethyl acetate was added to quench the reaction, washed with 10 mL of brine, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, and separated by column chromatography to obtain 9-(2,4-dimethyl Oxyphenyl)-9H-xanthene pure product 50mg, productive rate 83%, the molecular structural formula of gained 9-(2,4-dimethoxyphenyl)-9H-xanthene is

[0048]

[0049] figure 1 and figure 2 These are the NMR H spectrum and NMR C spectrum of 9-(2,4-dimethoxyphenyl)-9H-xanthene prepared in this example, respectively. figure 1 The chemical shifts of peaks in the hydrogen spectrum 1H NMR (400MHz, Chloroform-d) δ7.22-7....

Embodiment 2

[0051] Synthetic method of 9-(2,4,6-trimethoxyphenyl)-9H-oxygen / thioxanthene.

[0052]Take a 15mL pressure-resistant reaction tube, add DDQ 45mg, oxygen / thioxanthene 36mg, 1,3,5-trimethoxybenzene 101mg, molecular sieve 100mg, acetonitrile 2mL, open the reaction, and stir at room temperature for 12h. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, and 10 mL of brine was added for washing. The organic phase was separated, and the aqueous phase was extracted 3 times with ethyl acetate. The organic phases were combined and separated by column chromatography to obtain 9-(2,4,6- The pure product of trimethoxyphenyl)-9H-oxygen / thioxanthene was 65 mg, and the yield was 99%.

Embodiment 3

[0054] Synthetic method of 9-(2,4-dimethoxyphenyl)-9H-thioxanthene.

[0055] Take a 15mL pressure-resistant reaction tube, add 45mg of DDQ, 39mg of thioxanthene, 83mg of 1,3-dimethoxybenzene, 100mg of molecular sieves, 2mL of acetonitrile, open the reaction, and stir at room temperature for 12h. After the reaction, 10 mL of ethyl acetate was added to quench the reaction, washed with 10 mL of brine, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, and separated by column chromatography to obtain 9-(2,4-dimethyl The pure product of oxyphenyl)-9H-thioxanthene was 42mg, and the yield was 70%. The molecular structural formula of gained 9-(2,4-dimethoxyphenyl)-9H-thioxanthene is

[0056]

[0057] image 3 and Figure 4 These are the NMR H spectrum and NMR C spectrum of 9-(2,4-dimethoxyphenyl)-9H-thiaxanthene prepared in this example, respectively. image 3 The chemical shifts of the peaks in the hyd...

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Abstract

The invention discloses a synthesis method of a 9H-xanthene / thioxanthene compound. The 9H-xanthene / thioxanthene compound is obtained by dissolving a compound of a formula (I) and benzene substitutedby an electron-donating group with a solvent and then enabling reaction under the action of a water removing agent and a catalyst, and the 9H-xanthene / thioxanthene compound has a molecular structureshown by a formula (III), wherein Z represents an oxygen atom or a sulfur atom, R represents an aryl group substituted by an electron donating group. The synthesis method does not need metal catalysis, halogen addition, peroxide addition or high-temperature reaction conditions, is simple in reaction condition, high in yield and low in waste emission, is an environment-friendly method and is beneficial to energy conservation and environmental protection, reaction devices are simple, and industrial production is facilitated.

Description

technical field [0001] The present invention relates to the technical field of heterocyclic compounds, more specifically, to a method for synthesizing 9H-oxygen / thioxanthene compounds. Background technique [0002] Due to the wide application of oxygen / thioxanthene derivatives in biology, organic pigments and fluorescent materials, it has attracted a lot of attention. At the same time, 9H-oxygen / thioxanthene compounds are widely used in pharmaceutical intermediates (Nucleic Acids Res .1989,17,8135.; Tetrahedron Lett.,1988,29,577.), therefore, the introduction of this group has great research significance. [0003] However, usually the arylation of 9H-oxygen / thioxanthene compounds must be pre-functionalized by halogen (Org.Lett.2015, 17, 5096-5099; J.Am.Chem.Soc. ), or use transition metal reagents (RSC Adv., 2016, 6, 84748–84751) and peroxides (Angew. Chem. Int. Ed. 2013, 52, 13228–13232), and require higher reaction temperatures. This type of reaction is not conducive to ...

Claims

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Application Information

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IPC IPC(8): C07D311/82C07D335/12
CPCC07D311/82C07D335/12
Inventor 区颖聪陈迁霍延平王肖峰
Owner GUANGDONG UNIV OF TECH
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