A method for synthesizing benzothieno[3,2-b]chromones through ionic liquid-promoted intramolecular cross dehydrogenation coupling

A technology of chromone compounds and ionic liquids, applied in the direction of organic chemistry, can solve the problems of insufficient greenness and poor atom economy, and achieve the effect of simple operation, simple and mild conditions, and high reaction atom economy

Inactive Publication Date: 2017-05-24
XINJIANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention overcomes the synthetic benzothieno[3,2- b ] The traditional method of chromone compounds has the disadvantages of poor atom economy and insufficient greenness, and provides a kind of efficient and green synthesis using recyclable ionic liquid as accelerator, water as solvent, and cross-dehydrogenation coupling method as shown in the formula (II) Benzothieno[3,2- b ] chromone compound, wherein, the reaction process is as shown in the following reaction formula

Method used

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  • A method for synthesizing benzothieno[3,2-b]chromones through ionic liquid-promoted intramolecular cross dehydrogenation coupling
  • A method for synthesizing benzothieno[3,2-b]chromones through ionic liquid-promoted intramolecular cross dehydrogenation coupling
  • A method for synthesizing benzothieno[3,2-b]chromones through ionic liquid-promoted intramolecular cross dehydrogenation coupling

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 11 H -Benzo[4,5]thieno[3,2- b ] Synthesis of chromone

[0028]

[0029] Add the ionic liquid accelerator [Bmim]Br (0.1 mmol), 3-phenoxybenzothiophene-2-aldehyde (0.2 mmol) into the reaction tube, then add TBHP (0.2 mL) and water (0.05 mL) sequentially, at 100 oMagnetically stir the reaction at C for 24 hours, cool to room temperature after the reaction, add 2 mL of water, then extract with ethyl acetate (3 × 10 mL), combine the organic phases and dry with anhydrous sodium sulfate, filter, and remove under reduced pressure Ethyl acetate, product 1 was obtained by column chromatography (eluent polarity: petroleum ether / ethyl acetate 8: 1). Yield: 82%.

Embodiment 2

[0031] 11 H -Benzo[4,5]thieno[3,2- b ] Gram-level synthesis of chromone

[0032]

[0033] Add the ionic liquid accelerator [Bmim]Br (4 mmol), 3-aryloxybenzothiophene-2-aldehyde (8 mmol) into the reaction tube, then add TBHP (8 mL) and water (2 mL) in sequence, in 100 o The reaction was carried out under magnetic stirring at C for 24 hours, cooled to room temperature after the reaction, and the obtained solid was filtered with suction, and the crude product was separated by column chromatography to obtain product 1 (eluent polarity: petroleum ether / ethyl acetate 8 : 1). Yield: 80%.

Embodiment 3

[0035] 2-fluoro-11 H -Benzo[4,5]thieno[3,2- b ] Synthesis of chromone

[0036]

[0037] Add the ionic liquid promoter [Bmim]Br (0.1 mmol), 3-(4-fluorophenoxy)benzothiophene-2-aldehyde (0.2 mmol) into the reaction tube, then add TBHP (0.2 mL) and water in sequence (0.05 mL), at 100 o Magnetically stir the reaction at C for 24 hours, cool to room temperature after the reaction, add 2 mL of water, then extract with ethyl acetate (3 × 10 mL), combine the organic phases and dry with anhydrous sodium sulfate, filter, and remove under reduced pressure Ethyl acetate, product 2 was obtained by column chromatography (eluent polarity: petroleum ether / ethyl acetate 12:1). Yield: 77%; 1 H NMR (400 MHz, CDCl 3 ): δ 8.20 (d, J =8.0 Hz,1H), 8.03 (dd, J = 8.4, 3.2 Hz, 1 H), 7.93 (d, J = 8.4 Hz, 1 H), 7.70(dd, J = 9.2, 4.0 Hz, 1 H), 7.65-7.61 (m, 1 H), 7.56 (td, J = 7.2, 0.8 Hz,1H), 7.50 (ddd, J = 9.2, 7.6, 3.2 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ): δ 172.6(d, J CF = 2.2...

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Abstract

The invention discloses a method for using ionic liquid to promote intramolecular cross dehydrogenation coupling so as to synthesize benzothieno[3,2-b]chromone compounds. The method is characterized in that under a metal-free condition, water is used as solvent, the ionic liquid promotes the cross dehydrogenation coupling reaction of 3-aryloxybenzothiophene-2-aldehyde to effectively synthesize the benzothieno[3,2-b]chromone compounds, the reaction can be well performed under a gram-grade scale, and the activity of accelerator has no obvious declination after the accelerator is recycled for 5 times.

Description

technical field [0001] The invention belongs to the technical field of organic compound process application and relates to benzothieno[3,2- b ] Green synthesis of chromones. Background technique [0002] Chromone and its derivatives are a very important class of heterocyclic compounds, which have many biological and pharmaceutical activities, including: antibacterial, antifungal and antialgae activities. Among the many chromone derivatives, 11 H -Benzothieno[3,2- b ] Chromone compounds have been paid attention to by medicine and synthetic chemistry because of their low molecular weight and logP calculation value, which have good pharmaceutical and biological activities. Miller group (US20020183310A1) reported the synthesis of a series of benzothieno[3,2- b ] Chromone compounds and the activity test of the compounds, found that the compounds are a series of novel β estrogen receptor (Estrogen Receptor beta, ERβ) selective ligands. However, this synthesis method uses base...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 刘晨江刘文博
Owner XINJIANG UNIVERSITY
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