Preparation method of naphthofuran derivative

A technology for furan derivatives and naphthol is applied in the field of preparation of naphthofuran derivatives and achieves the effects of good regioselectivity, low cost and few side reactions

Active Publication Date: 2019-04-05
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, titanium tetrachloride is used as a dehydrating agent for naphthofuran derivatives, and there is no bibliographical information at present.

Method used

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  • Preparation method of naphthofuran derivative
  • Preparation method of naphthofuran derivative
  • Preparation method of naphthofuran derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of naphthofuran derivative IIIa

[0025]

[0026] In a 50 mL two-necked flask equipped with a reflux condenser and under nitrogen protection, add β-naphthol Ia (2 mmol) and hexafluoroisopropanol (10 mL), and heat to reflux while stirring. After the β-naphthol Ia was completely dissolved, titanium tetrachloride (2mmol) was added, and finally a mixed solution of α-haloketone IIa (2mmol) and hexafluoroisopropanol (2mL) was slowly added dropwise, and the reflux reaction was continued. The reaction process was monitored by TLC. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product IIIa as a yellow oil with a yield of 76%.

[0027] 1 H NMR (600MHz, C...

Embodiment 2

[0028] Embodiment 2: the synthesis of naphthofuran derivative III'a

[0029]

[0030] In a 50mL two-necked flask equipped with a reflux condenser and under nitrogen protection, α-naphthol I'a (2mmol) and trifluoroethanol (15mL) were added, and heated to reflux while stirring. After α-naphthol was completely dissolved, titanium tetrachloride (3mmol) was added, and finally a mixed solution of α-haloketone IIa (3mmol) and trifluoroethanol (2mL) was slowly added dropwise, and the reflux reaction was continued. TLC monitoring. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product III'a as a yellow oil with a yield of 78%.

[0031] 1 H NMR (600MHz, CDCl 3 )δ8.27(d, J=8.2Hz, 1H), 7.91...

Embodiment 3

[0032] Embodiment 3: the synthesis of naphthofuran derivative IIIb

[0033]

[0034] β-Naphthol Ib (2 mmol) and trifluoroethanol (10 mL) were added to a 50 mL two-neck flask under nitrogen protection with a reflux condenser installed, and heated to reflux while stirring. After the β-naphthol Ib was completely dissolved, titanium tetrachloride (4mmol) was added, and finally a mixed solution of α-haloketone IIa (3mmol) and trifluoroethanol (2mL) was slowly added dropwise, and the reflux reaction was continued. Monitored by TLC. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product IIIb as a yellow oil with a yield of 89%.

[0035] 1 H NMR (600MHz, CDCl 3 )δ8.06(d, J=1.8Hz, 1H), 7...

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Abstract

The invention discloses a method for efficiently synthesizing a naphthofuran derivative from naphthol and an alpha-haloketone under the action of titanium tetrachloride by one step. The method specifically includes adding the naphthol and polyfluoroalcohol under the protection of an inert gas, heating and stirring the mixture until reflux, adding the titanium tetrachloride, dropwise adding a mixedsolution of the alpha-haloketone and the polyfluoroalcohol, and performing separation and purification after the reaction to obtain the naphthofuran derivative. The synthesis method has the advantages of easiness in acquisition of raw materials, low cost, mild reaction condition, simplicity and controllability in operation, less side reaction, simple post-treatment, high product yield, greatly reduced production cost, good economic benefit, and suitability for industrialized mass production.

Description

technical field [0001] The invention relates to a method for preparing naphthofuran derivatives, in particular to a method for efficiently synthesizing naphthofuran derivatives in the next step under the action of titanium tetrachloride by using naphthol and α-halogenated ketone as raw materials. Background technique [0002] Many natural products and synthetic drugs contain naphthofuran core skeletons, and molecules with these skeletons usually exhibit unique biological properties, such as antibacterial, antifungal, antioxidative, and cytotoxic. Furomolugin isolated from Trichinella cuneiformis can inhibit the peroxidation of mitochondrial and microsomal membrane lipids (Org.Lett.2005, 7(9), 1765-1768.), Xylarianaphthol- 1 exhibits certain anticancer activity (Bioorg.Med.Chem.Lett.2014, 24(15), 3389-3391.) Rubicordifolin isolated from Rubidis has significant cytotoxic activity (J.Am.Chem.Soc. 2005, 127(9), 2870-2871.), Balsaminones A isolated from the peel of Impatiens sho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07D307/93C07J73/00
CPCC07D307/92C07D307/93C07J73/003
Inventor 唐强罗娟
Owner CHONGQING MEDICAL UNIVERSITY
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