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Method for synthesizing 3-hydroxyl oxoindole derivative

A technology of indole derivatives, hydroxyl oxidation, applied in organic chemistry and other directions

Active Publication Date: 2017-04-19
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, using indole as a simple and easy-to-obtain raw material, there is no method for the synthesis of 3-hydroxyindole skeleton under metal-free and catalyst-free conditions.

Method used

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  • Method for synthesizing 3-hydroxyl oxoindole derivative
  • Method for synthesizing 3-hydroxyl oxoindole derivative
  • Method for synthesizing 3-hydroxyl oxoindole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074]

[0075] In this example: R 1 is methyl; R 2 is hydrogen; R 3 for hydrogen.

[0076] Step: In a 10mL reaction flask, add compound I-1 (0.3mmol, 62.8mg), iodobenzene diacetate (0.6mmol, 193mg) and acetic acid (2mL) to react at 80°C, TLC (with thin layer chromatography Chromatography) was detected until the reaction was complete. Post-processing purification: the reaction mixture was washed with saturated sodium bicarbonate (20 mL×2), extracted with ethyl acetate (20 mL×2), the organic phases were combined, and washed with saturated NaCl (20 mL×1). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 1-10: 1, the present embodiment preferably V ( Petroleum ether): V (ethyl acetate) = 3:1], the pure product was obtained as a white solid, the yield: 78%.

[0077] Compound II-1 was tested:

[0078] Melting p...

Embodiment 2

[0084]

[0085] In this example: R 1 is methyl; R 2 is 4-methyl; R 3 for hydrogen.

[0086] Step: In a 10mL reaction flask, add compound I-2 (0.3mmol, 67mg), iodobenzene diacetate (0.6mmol, 193mg) and acetic acid (2mL) to react at 80°C, TLC (with thin layer chromatography method) until the reaction was complete. Post-processing purification: the reaction mixture was washed with saturated sodium bicarbonate (20 mL×2), extracted with ethyl acetate (20 mL×2), the organic phases were combined, and washed with saturated NaCl (20 mL×1). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 1-10: 1, the present embodiment preferably V ( Petroleum ether): V (ethyl acetate) = 3:1], the pure product was obtained, white solid, yield: 55%.

[0087] Compound II-2 was tested:

[0088] Melting point: 156-157°C

[0089] 1 H ...

Embodiment 3

[0094]

[0095] In this example: R 1 is methyl; R 2 For 4-benzyloxy; R 3 for hydrogen.

[0096] Step: In a 10mL reaction flask, add compound I-3 (0.3mmol, 94.6mg), iodobenzene diacetate (0.6mmol, 193mg) and acetic acid (2mL) to react at 80 ° C, TLC (with thin layer chromatography Chromatography) was detected until the reaction was complete. Post-processing purification: the reaction mixture was washed with saturated sodium bicarbonate (20 mL×2), extracted with ethyl acetate (20 mL×2), the organic phases were combined, and washed with saturated NaCl (20 mL×1). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 1-10: 1, the present embodiment preferably V ( Petroleum ether): V (ethyl acetate) = 3:1], the pure product was obtained as a white solid, the yield: 62%.

[0097] Compound II-3 was tested:

[0098] Mel...

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Abstract

The invention discloses a method for synthesizing a 3-hydroxyl oxoindole derivative. The synthetic route is as shown in the specification, wherein R1 is methyl, ethyl, propyl, butyl, isopropyl, cyclohexyl, allyl, benzyloxyethyl or n-butyric acid methyl ester; a substituent R2 is methyl, methoxy, benzyloxy, fluorine, chlorine or bromine; and a substituent R3 is methyl, bromine or phenyl. The synthetic process comprises the following steps: dissolving a compound I and iodobenzene diacetate in acetic acid and reacting completely at 40-100 DEG C, and postprocessing and purifying to obtain a product II. The raw materials used in the method are easy to prepare, and iodobenzene diacetate can be sold in the market; there is no need to use a catalyst such as a metal catalyst or an organic catalyst, and cost is reduced and the method is environment-friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 3-hydroxyindole derivatives. Background technique [0002] 3-Hydroxyindole and its derivatives are very important structural units, which widely exist in many natural products and pharmaceutical active molecules, and are a class of dominant skeletons that have attracted extensive attention from synthetic chemists. For example: maremycins A ~ B have anti-cytotoxicity to human leukemia cells K562. The natural products Convolutamydines A-E isolated from the marine bryozoan Amathia convoluta in Florida by Kamano's group have potential anti-tumor activity. Especially when Convolutamydines A inhibits the differentiation of human promyelocytic leukemia cells HL-60, the half-inhibitory concentration (IC50) of Convolutamydine A can reach 0.1 μg·mL -1 , while the half-inhibitory concentration of Convolutamydine B was 12.5 μg·mL -1 , In addition, SM-130686 is a ...

Claims

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Application Information

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IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 王亮瞿星胡思前刘继延
Owner JIANGHAN UNIVERSITY
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