A kind of synthetic method of polybenzo five-membered aromatic heterocyclic coumarin condensed heterocyclic compound

A synthesis method and compound technology, applied in the field of heterocyclic compound synthesis, can solve the problems of high toxicity of reagents, harsh reaction conditions, inconvenient source of raw materials, etc., and achieve the effects of good substrate adaptability and high group tolerance.

Inactive Publication Date: 2021-05-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing synthetic methods have disadvantages such as inconvenient sources of raw materials, high toxicity of reagents, or the use of metal catalysts or oxidants, harsh reaction conditions, and easy pollution to the environment.

Method used

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  • A kind of synthetic method of polybenzo five-membered aromatic heterocyclic coumarin condensed heterocyclic compound
  • A kind of synthetic method of polybenzo five-membered aromatic heterocyclic coumarin condensed heterocyclic compound
  • A kind of synthetic method of polybenzo five-membered aromatic heterocyclic coumarin condensed heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthetic compound 1~18

[0034] Add 3-(2-furyl)-4-(phenyl)coumarin into the light tube, and use ethanol as solvent to prepare a solution with a concentration of 0.0025mol / L. Under protected conditions, after 2 hours of ultraviolet light irradiation by a 500W high-pressure mercury lamp, the solvent was recovered by distillation under reduced pressure, and it was separated and purified by silica gel column chromatography (petroleum ether:ethyl acetate=50:1) to obtain the compound 1 pure product.

[0035] In this embodiment, with equimolar 3-(2-furyl)-4-(4-methylphenyl) coumarin, 3-(2-furyl)-4-(4-ethylphenyl) Coumarin, 3-(2-furyl)-4-(4-fluorophenyl)coumarin, 3-(2-furyl)-4-(4-chlorophenyl)coumarin, 3-(2-furyl)-4-(4-trifluoromethylphenyl)coumarin, 3-(2-benzofuryl)-4-(4-methylphenyl)coumarin, 3-(2-benzofuryl)-4-(4-methoxyphenyl)coumarin, 3-(2-benzofuryl)-4-(4-fluoro)coumarin, 3 -(2-thienyl)-4-(phenyl)coumarin, 3-(2-thienyl)-4-(4-methylphenyl)coumarin, 3-(2-thienyl)- 4-(...

Embodiment 2

[0065] In this example, an equal volume of methanol was used to replace the ethanol in Example 1, and other steps were the same as in Example 1 to obtain compounds 1-18, and the yields of each compound are shown in Table 4.

[0066] Table 4 is the productive rate of compound 1~18 when methanol is solvent

[0067] Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 50％ 55％ 53％ 36％ 31％ 43％ Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 55％ 68％ 56％ 54％ 62％ 71％ Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 36％ 29％ 57％ 40％ 65％ 45％

Embodiment 3

[0069] In this example, an equal volume of acetonitrile was used to replace the ethanol in Example 1, and other steps were the same as in Example 1 to obtain compounds 1-18. The yields of each compound are shown in Table 5.

[0070] Table 5 is the productive rate of compound 1~18 when acetonitrile is solvent

[0071] Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 40％ 44％ 43％ 31％ 29％ 33％ Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 43％ 50％ 52％ 51％ 55％ 63％ Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 32％ 26％ 50％ 50％ 53％ 39％

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Abstract

The invention discloses a method for synthesizing polybenzo five-membered aromatic heterocyclic coumarin condensed heterocyclic compounds. The method uses 3-arylhetero-4-phenylcoumarin compounds as raw materials and ethanol as Solvent, the compound of the present invention can be obtained by ultraviolet light irradiation under mild conditions. The synthesis method of the present invention does not need the addition of any oxidant, additive and catalyst; ethanol is used as a reaction solvent, which is green and friendly; and exhibits better substrate adaptability, group tolerance and higher atom utilization. The compounds synthesized in the invention all have photoluminescent properties, are photoluminescent materials, and can be printed on paper as various anti-counterfeit marks for anti-alteration or forgery, and can also be used as road sign lights at night.

Description

technical field [0001] The invention belongs to the technical field of synthesis of heterocyclic compounds, in particular to a method for synthesizing heterocyclic compounds containing five-membered rings and six-membered rings without hydrogenation, having oxygen atoms or sulfur atoms as ring heteroatoms and fused with other rings . Background technique [0002] As an important class of organic heterocyclic compounds, coumarin has various physiological activities such as antibacterial, antitumor, and antioxidative, and has been widely used in the pharmaceutical industry. Coumarin derivatives have drug activities such as analgesia, insecticide, blood pressure lowering, antithrombotic and anticancer. In addition, such molecules are also used in the fields of fluorescent dyes, organic optoelectronic materials and molecular fluorescent probes. At present, the market demand for high-efficiency and low-toxic coumarin compounds and their derivatives is increasing day by day, whi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07D495/04C09K11/06C09K9/02
CPCC07D493/04C07D495/04C09K9/02C09K11/06C09K2211/1088C09K2211/1092
Inventor 张尊听史娟王涛贺云
Owner SHAANXI NORMAL UNIV
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