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Method for preparing 2,5-disubsituted furan compound

A compound and disubstitution technology, applied in the field of preparation of furan compounds, can solve the problems of harsh reaction conditions, high synthesis cost, and long steps of 1,4-dicarbonyl compounds, and achieve the effect of low cost and simple operation

Active Publication Date: 2018-12-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the most classic method of synthesizing 2,5-disubstituted furan is to use 1,4-dicarbonyl compound condensation ring-closing synthesis (Paal-Knoor reaction), but the synthesis of 1,4-dicarbonyl compound with a slightly complicated structure takes a long time. high cost
Or use alkenes and alkynes as substrates and prepare them by transition metal-catalyzed cyclization reactions. Because of the need for transition metal catalysis, the reaction conditions are relatively harsh and the synthesis cost is high.

Method used

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  • Method for preparing 2,5-disubsituted furan compound
  • Method for preparing 2,5-disubsituted furan compound
  • Method for preparing 2,5-disubsituted furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A multi-substituted furan compound, the preparation method is as follows:

[0026] Add 50-80mL of chlorobenzene into a 250mL single-necked flask, then add 10mmol of tert-butyraldehyde and 10mmol of Reflux at 100°C for 12 hours, remove the solvent under reduced pressure to obtain a crude product, and then separate the product by flash column chromatography 41.6 mg (81%). The structure of the product characterizes the physical constants: 1 H NMR (400MHz, CDCl 3 )δ7.42-7.34(m,2H),7.31-7.27(m,1H),7.21-7.18(m,2H),6.53(d,J=3.4Hz,1H),5.85(d,J=3.4Hz ,1H),3.41(s,3H),0.97(s,9H); 13 C NMR (100MHz, CDCl 3 )δ166.57, 159.66, 145.92, 144.91, 129.43, 127.27, 127.19, 117.85, 103.84, 38.61, 32.70, 28.55.

Embodiment 2

[0028] Add 50-80mL of chlorobenzene into a 250mL single-necked flask, then add 10mmol of tert-butyraldehyde and 10mmol of Reflux at 100°C for 12 hours, remove the solvent under reduced pressure to obtain a crude product, and then separate the product by flash column chromatography 28.8 mg (74%). The structure of the product characterizes the physical constants: 1 H NMR (400MHz, CDCl 3 )δ6.93(d, J=3.4Hz, 1H), 6.06(d, J=3.4Hz, 1H), 3.19(br, 6H), 1.30(s, 9H); 13 C NMR (100MHz, CDCl 3 )δ166.12, 160.71, 146.55, 117.33, 104.09, 32.98, 29.04.

Embodiment 3

[0030] Add 50-80mL of chlorobenzene into a 250mL single-necked flask, then add 10mmol of tert-butyraldehyde and 10mmol of Reflux at 100°C for 12 hours, remove the solvent under reduced pressure to obtain a crude product, and then separate the product by flash column chromatography 33.4 mg (75%). The structure of the product characterizes the physical constants: 1 H NMR (400MHz, CDCl 3 )δ6.97(d, J=3.4Hz, 1H), 6.05(d, J=3.4Hz, 1H), 3.56(br, 4H), 1.30(s, 9H), 1.25(br, 6H); 13 C NMR (100MHz, CDCl 3 )δ165.84, 159.80, 147.09, 117.34, 104.15, 32.94, 29.05.

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Abstract

The invention discloses a method for preparing a 2,5-disubsituted furan compound. The method comprises the following steps of adding RCHO, 2-acylfuran, an initiator and a catalyst into an organic solvent, and performing reflux reaction, so as to obtain the 2,5-disubsituted furan compound, wherein the molar ratio of the RCHO to the 2-acylfuran is 100:1 to 1:100; the molar ratio of the RCHO to the initiator is 100:1 to 1:100; the molar ratio of the RCHO to the catalyst is 100:1 to 1:100. The method for preparing the 2,5-disubsituted furan compound has the advantages that the strict anhydrous condition is not required, and the strong alkaline is not required; the operation is simple and convenient, the cost is low, and the like.

Description

technical field [0001] The invention relates to a method for preparing multi-substituted furan compounds, in particular to a method for preparing 2,5-disubstituted furan compounds. Background technique [0002] As a typical representative of five-membered heterocycles, the furan ring widely exists in natural products and continues to attract the attention of the organic synthesis community because of its inherent biological activity. Recent studies have shown that multi-substituted furan compounds have good effects in antiviral, antibacterial, antitumor, anti-inflammatory and insecticidal. Multi-substituted furans are not only natural products and structural units of important medicines, but also important intermediates in organic synthesis, used as raw materials for pesticides, medicines, spices and dyes. [0003] At present, the most classic method of synthesizing 2,5-disubstituted furan is to use 1,4-dicarbonyl compound condensation ring-closing synthesis (Paal-Knoor rea...

Claims

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Application Information

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IPC IPC(8): C07D307/68C07D307/46
CPCC07D307/46C07D307/68C07B2200/07
Inventor 尹标林罗文坤
Owner SOUTH CHINA UNIV OF TECH
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