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Preparation method of 2,5-disubstituted furan derivatives

A furan derivative and disubstituted technology, applied in 2 fields, can solve problems such as unsatisfactory effect on regio and stereoselectivity, and achieve the effects of good regioselectivity, wide substrate range and high yield

Active Publication Date: 2019-08-20
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the synthesis of 2,5-disubstituted furan is one of the important contents of organic chemistry, and wherein, the synthetic method of 2,5-disubstituted furan in the prior art is still not quite as effective in regio and stereoselective satisfactory

Method used

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  • Preparation method of 2,5-disubstituted furan derivatives
  • Preparation method of 2,5-disubstituted furan derivatives
  • Preparation method of 2,5-disubstituted furan derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 2-phenyl-5-o-tolylfuran

[0025]

[0026] 0.15 mmol of lithium tert-butoxide, 0.1 mmol of 1,3-diphenyl-1,3-propanedione, 0.005 mmol of p-cymene dichloride ruthenium (II) dimer, 2,4, 0.15 mmol of 6-trimethylbenzoic acid, 0.2 mmol of 2-(dimethyl(oxo)-λ6sulfanyl)-1-(o-tolyl)ethan-1-one, and 2 mL of toluene were added to 15 mL of reaction tube, placed in an oil bath at 120°C, and reacted under an air atmosphere for 24 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 16.9 mg of the target product with a yield of 73%. The NMR and high-resolution mass spectrometry of this target product are characterized as follows: 1 H NMR (500MHz, Chloroform-d) δ7.81(d, J=7.8Hz, 1H), 7.78-7.75(m, 2H), 7.42(t, J=7.8Hz, 2H), 7.33-7.25(m, 3H), 7.27-7.20(m, 1H), ...

Embodiment 2

[0028] Preparation of 2-(3-chlorophenyl)-5-phenylfuran

[0029]

[0030] 0.15 mmol of lithium tert-butoxide, 0.1 mmol of 1,3-diphenyl-1,3-propanedione, 0.005 mmol of p-cymene dichloride ruthenium (II) dimer, 2,4, 0.15mmol of 6-trimethylbenzoic acid, 0.2mmol of 1-(3-chlorophenyl)-2-(dimethyl(oxo)-λ6sulfanyl)ethan-1-one, and 2mL of toluene were added to 15mL placed in an oil bath at 120°C, and reacted for 24 hours in an air atmosphere; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by thin layer chromatography to obtain 11.9 mg of the target product with a yield of 47%. The NMR and high-resolution mass spectrometry of this target product are characterized as follows: 1 H NMR (500MHz, Chloroform-d) δ7.77-7.74 (m, 2H), 7.73 (t, J=1.9Hz, 1H), 7.61 (m, 1H), 7.45-7.40 (m, 2H), 7.35- 7.28(m, 2H), 7.25-7.22(m, 1H), 6.78-...

Embodiment 3

[0032] Preparation of 2-(4-methoxyphenyl)-5-phenylfuran

[0033]

[0034] 0.15 mmol of lithium tert-butoxide, 0.1 mmol of 1,3-diphenyl-1,3-propanedione, 0.005 mmol of p-cymene dichloride ruthenium (II) dimer, 2,4, 0.15mmol of 6-trimethylbenzoic acid, 0.2mmol of 2-(dimethyl(oxo)-λ6sulfanyl)-1-(4-methoxyphenyl)ethan-1-one, and 2mL of toluene were added Put it into a 15mL reaction tube, place it in an oil bath at 120°C, and react for 24h under an air atmosphere; cool to room temperature, dilute the reaction solution with ethyl acetate, wash three times with water, and wash the organic phase with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 11.8 mg of the target product with a yield of 47%. The NMR and high-resolution mass spectrometry of this target product are characterized as follows: 1 H NMR (500MHz, Chloroform-d) δ7.75-7.72(m, 2H), 7.71-7.67(m, 2H), 7.40(t, J=7.8Hz, 2H), 7.30-7.22(m, 1H), 6.97-6.94(m, 2H), 6....

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Abstract

The invention discloses a preparation method of 2,5-disubstituted furan derivatives. One carbon-carbon bond is cut off, at the same time, a novel carbon-carbon bond is established, cyclization reactions are carried out to obtain the 2,5-disubstituted furan derivatives, which have good regioselectivity. The method has the advantages of easily available raw materials, high yield, mild reaction conditions, short reaction time, wide substrate range, strong reaction specificity, and convenient and green post-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2,5-disubstituted furan derivatives. Background technique [0002] 2,5-disubstituted furan is one of the basic organic structural units, and it also widely exists in natural products, and is also an important intermediate in industrial organic synthesis, widely used in many fields such as medicine, food spices, and pesticides. For example, furazolidonum (furazolidonum), which has significant antibacterial activity, has obvious drug activity against enteritis, bacillary dysentery and colon cancer and other intestinal infection diseases. Active and environmentally friendly, it is widely used in agriculture. Therefore, the synthesis of 2,5-disubstituted furan is one of the important contents of organic chemistry, and wherein, the synthetic method of 2,5-disubstituted furan in the prior art is still not quite as effective in regio and st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/36C07D307/38C07D307/42C07D409/04
CPCC07D307/36C07D307/38C07D307/42C07D409/04Y02P20/584Y02A50/30
Inventor 程国林文思
Owner HUAQIAO UNIVERSITY
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