Benzofuran derivative and preparation method thereof

A technology for benzofuran and derivatives, which is applied in the field of benzofuran derivatives and their preparation, can solve the problems of limited number of separation and extraction, low content of benzofuran compounds, etc., and achieve short reaction time and cheap reagents , the effect of high atom economy

Active Publication Date: 2016-09-21
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] It is precisely because many natural benzofuran compounds show good biological activity, but the content of benzofuran compounds containing multiple substituents in natural products is relatively small, and the number of separation and extraction is limited, and its output cannot satisfy people at all. needs

Method used

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  • Benzofuran derivative and preparation method thereof
  • Benzofuran derivative and preparation method thereof
  • Benzofuran derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] A benzofuran derivative, the structural formula of the benzofuran derivative is:

[0044]

[0045] A preparation method of benzofuran derivatives, said preparation method comprising the following steps:

[0046] (1) With 830mmol of sodium hydride as a catalyst, 200mmol of diisopropyl malonate and 440mmol of propargyl bromide were added to 210mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, Spin-dried under reduced pressure to obtain a yellow-brown solid product, namely compound a-1;

[0047] (2) Mix 80mmol compound a-1 with 200mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as the base, 150mL of anhydrous acetonitrile as the solvent, stirred and reacted at 20°C for 12 hours, the product was washed with water, extracted wi...

Embodiment 2

[0053] A benzofuran derivative, the structural formula of the benzofuran derivative is:

[0054]

[0055] A preparation method of benzofuran derivatives, said preparation method comprising the following steps:

[0056] (1) With 960mmol sodium hydride as a catalyst, 200mmol diethyl malonate and 600mmol propargyl bromide were added to 140mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 5 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a yellow-brown solid product, namely compound a-2;

[0057] (2) Mix 80mmol compound a-2 with 240mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (1.92mmol / 0.64mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 384mmol triethylamine as the base and 100mL anhydrous acetonitrile as the solvent, stirred and reacted at 25°C for 14 hours, the product was washed with water, extracted with ethyl acetate, spin-drie...

Embodiment 3

[0063] A benzofuran derivative, the structural formula of the benzofuran derivative is:

[0064]

[0065] A preparation method of benzofuran derivatives, said preparation method comprising the following steps:

[0066] (1) Using 900mmol of sodium hydride as a catalyst, 200mmol of diisopropyl malonate and 500mmol of propargyl bromide were added to 160mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 7.5 hours, the product was washed with water, extracted with ethyl acetate, Spin-dried under reduced pressure to obtain a yellow-brown solid product, namely compound a-3;

[0067] (2) Mix 80mmol compound a-3 with 224mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (3.84mmol / 1.28mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 360mmol triethylamine as the base and 135mL anhydrous acetonitrile as the solvent, stirred and reacted at room temperature for 10 hours, the product was washed with wate...

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Abstract

The invention discloses a benzofuran derivative and a preparation method thereof. A benzofuran compound is prepared from different multi-alkyne substrates by a cascade reaction. The reaction overcomes the defects of excessively long path, harsh substrate and reaction condition requirements, limited expansion of substituted functional groups and the like in a conventional reaction; the reaction not only is simple in substrate synthesis and relatively low in price of reagents, but also has high atom economy, obtains target molecules in a green and environmental-friendly manner, and provides a valuable approach for industrial production of benzofuran.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to a benzofuran derivative and a preparation method thereof. Background technique [0002] Benzofuran compounds have strong biological activity, and traces of such compounds can be found in a large number of natural and non-natural products. It is precisely because of the wide range of pharmacological activities of benzofuran compounds and their derivatives and the ubiquity in nature that these compounds have attracted people's close attention. [0003] Natural benzofuran compound 1, because of its structural skeleton of 2-aryl substituted benzofuran, exhibits good biological activities such as protecting ischemic tissue reperfusion, inhibiting thrombus formation and anti-platelet aggregation, etc. The compound will have a place in the treatment of cardiovascular and other diseases. Scammells et al. designed and synthesized a series of analogs 2-4 using it as a lead co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/77
CPCC07D307/77
Inventor 姚亮亮胡奡胡益民
Owner ANHUI NORMAL UNIV
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