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Preparation method of benzofuran derivative

A technology of benzofuran and derivatives, applied in the field of organic chemical synthesis, can solve the problems of complex reaction system, high reaction temperature, metal ion waste water and the like

Inactive Publication Date: 2020-10-30
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic raw materials of this method are convenient and easy to obtain, and the operation is simple, but its reaction system is complex, the reaction temperature is high, and Cu 2+ As a catalyst, a large amount of metal ion wastewater will be produced, causing environmental pollution

Method used

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  • Preparation method of benzofuran derivative
  • Preparation method of benzofuran derivative
  • Preparation method of benzofuran derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of o-hydroxystilbene and its derivatives

[0055] O-hydroxystilbene and its derivatives can be purchased from the market or prepared. In this example, o-hydroxystilbene and its derivatives were synthesized by using the McMurry method. The reaction equation is as follows:

[0056]

[0057] Among them, R 1 , R 2 , R 3 , R 4 , R 1 ’, R 2 ’, R 3 ’, R 4 ’, R 5 'is an aryl group, an acid (amine) group, a carboxylic acid (ester) group, a sulfonic acid (amine, ester) group, a sulfinic acid (amine, ester) group, a nitrile group, a (cyclo) alkyl group, an alkenyl group, an alkyne group Any one of halogen, alkoxy, amino, amino, thioether, nitro, silicon, and phosphonic acid (ester) groups.

[0058] The specific preparation method is as follows: adding zinc powder and a stirring bar into a pre-dried two-neck flask, sealing and degassing, and adding anhydrous tetrahydrofuran under the protection of argon. The solution was cooled to -5°C, at whic...

Embodiment 2

[0061] Example 2: Preparation of a 2-arylbenzofuran compound

[0062] In a 15mL single-port reaction tube, add 10mg (0.05mmol) (E)-2-styrylphenol (structure as figure 1 S in 1 shown) and 24 μL (0.1 mol) of dodecylmercaptan, stirred and reacted at 140° C. for 48 h under an oxygen atmosphere. Add 1 mL of water to quench the reaction, extract with ethyl acetate (3 times×2 mL / time), and combine the organic phases. After drying the organic phase with anhydrous sodium sulfate, the organic phase was distilled off under reduced pressure to remove the solvent, and the residue was separated through a 200-300 mesh silica gel column, and the eluent was PE:EA=10:1 (v / v, implemented later) Examples are all volume ratios, no more details), to obtain the target product, the structure is as figure 2 T in 1 shown. Obtain the target product T 1 6.5 mg, yield 65%. The reaction formula is as follows:

[0063]

[0064] Target product T 1 It is a white solid, and its spectral data are a...

Embodiment 3

[0066] Example 3: Preparation of another 2-arylbenzofuran compound

[0067] In a 15mL single-port reaction tube, add 10mg (0.044mmol) of (E)-2-(4-methoxystyryl)phenol (structure as figure 1 S in 2 shown) and 21 μL (0.088 mmol) of dodecylmercaptan, stirred at 140° C. for 48 h under an oxygen atmosphere. Add 1 mL of water to quench the reaction, extract with ethyl acetate (3 times × 2 mL / time), combine the organic phases, dry the organic phases with anhydrous sodium sulfate, distill off the solvent under reduced pressure, and separate the residue through a 200-300 mesh silica gel column , the eluent is PE:EA=10:1, the target product is obtained, the structure is as figure 2 T in 2 shown. Obtain the target product T 2 4.7 mg, yield 47%. The reaction formula is as follows:

[0068]

[0069] Target product T 2 It is a white solid, and its spectral data are as follows:

[0070] 1 H NMR (600MHz, CDCl 3 ): δ7.80(d, J=8.8Hz, 2H), 7.55(d, J=7.5Hz, 1H), 7.50(d, J=8.1Hz, 1...

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Abstract

The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of a benzofuran derivative. According to the specific technical scheme, the preparation method of the benzofuran derivative comprises the following steps: taking o-hydroxystilbene or a derivative thereof as a raw material, taking mercaptan as a catalyst, and reacting in an atmosphereor oxygen environment to obtain the benzofuran derivative. The method provided by the invention has the advantages of cheap and easily available substrate, good adaptability, mild and simple synthesisconditions, no need of using a solvent, atmosphere or oxygen as an oxidant, greenness and environmental protection.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a preparation method of benzofuran derivatives. Background technique [0002] Benzofuran, also known as oxyindene, is a heterocyclic aromatic hydrocarbon organic compound composed of condensed benzene ring and furan ring. It is a colorless liquid at room temperature and is a component of coal tar. The molecular structural formula of benzofuran is as follows: [0003] [0004] 2-Arylbenzo[b]furan compounds, as a heterocyclic compound with benzo[b]furan skeleton, have various biological activities, such as antitumor, antifungal, antioxidative, anti-inflammatory, antiplatelet aggregation , anti-proliferation, anti-virus, cancer prevention, immune response suppression, insecticide, phytoestrogens, etc.; widely used in the treatment of cancer, central nervous system, mental illness, diabetes and other diseases. Although 2-arylbenzofuran compounds have been fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79C07D307/80
CPCC07D307/79C07D307/80
Inventor 王淳张国林万顺莉
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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