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Green synthesis of indole compounds

A technology of green synthesis and synthesis method, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problem of unfriendly solvents, strong corrosion of equipment, and catalyst dosage Large and other problems, to achieve the effect that the product yield is not affected, the product purity is good, and the cost is low

Active Publication Date: 2009-08-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve a series of problems in the prior art of preparing indole compounds, such as large amount of catalyst used, strong corrosion of equipment, unfriendly solvents to the environment, cumbersome operation, etc., and follow a more green and efficient synthesis concept, the present invention The purpose of this paper is to disclose a method for synthesizing indole compounds with disulfonic acid-type acidic ionic liquids as catalysts and water instead of traditional organic solvents

Method used

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  • Green synthesis of indole compounds
  • Green synthesis of indole compounds
  • Green synthesis of indole compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Double sulfonic acid type acidic ionic liquid [(HSO 3 -p) 2 im][HSO 4 ](2.5mmol) was added to a 25ml double-necked round bottom flask containing water (15ml), and mechanically stirred into a homogeneous ionic liquid aqueous solution, cyclohexanone (0.490g, 5mmol) and phenylhydrazine (0.540g, 5mmol) in sequence Add to the reaction vessel, under mechanical stirring, heat in an oil bath at 70°C, keep the temperature for 0.5h, and cool to room temperature. The mixture is directly filtered and dried to obtain 0.83g of 1,2,3,4-tetrahydrocarbazole. The yield is 93%, and the product structure is:

[0033]

Embodiment 2

[0035] Double sulfonic acid type acidic ionic liquid [(HSO 3 -p) 2 im][HSO 4 ](2.5mmol) was added to a 25ml double-necked round bottom flask filled with water (30ml), mechanically stirred evenly into a homogeneous ionic liquid aqueous solution, cyclohexanone (0.490g, 5mmol) and phenylhydrazine (0.540g, 5mmol) in sequence Add to the reaction vessel, under mechanical stirring, heat in an oil bath at 70°C, keep the temperature for 1 hour, cool to room temperature, directly filter and dry the mixture to obtain 0.76 g of 1,2,3,4-tetrahydrocarbazole. The rate is 87%, and the product structure is:

[0036]

Embodiment 3

[0038] Double sulfonic acid type acid ionic liquid [(HSO 3 -p) 2 im][HSO 4 ](2.5mmol) was added to a 25ml double-necked round bottom flask containing water (15ml), and mechanically stirred into a homogeneous ionic liquid aqueous solution, cyclohexanone (0.490g, 5mmol) and phenylhydrazine (0.540g, 5mmol) in sequence Add to the reaction vessel and react at room temperature for 12 hours under mechanical stirring. The mixture is directly filtered and dried to obtain 0.83 g of 1,2,3,4-tetrahydrocarbazole with a yield of 90%. The product structure is:

[0039]

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Abstract

The invention discloses a green synthetic method for indole compounds. The synthetic method uses aldehyde or ketone and aromatic polyhydrazide as substrates, the aldehyde or the ketone and the aromatic polyhydrazide are fully reacted at a temperature between 20 and 100 DEG C in a water solvent under the catalysis of disulfonic acid type ionic liquid, and the obtained reaction mixture is filtered and dried to obtain the indole compounds. The preparation method has mild reaction conditions, simple and convenient operation, easy separation for products and environment protection during synthesis; the obtained indole compounds have high purity; the catalyst can be repeatedly used; and the method is the green synthetic method, and is suitable for industrialized production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing indole compounds (2) Background technology [0002] Indole compounds have important uses in the fields of medicine and pesticides. Especially in recent years, indole alkaloids have been frequently used in anti-tumor drugs. There are many methods to synthesize indole compounds. Fischer indole synthesis method is considered to be one of the most convenient and economical methods, and has a wide range of applications in indole synthesis. In the traditional Fischer indole synthesis method, sulfuric acid, hydrochloric acid, trifluoroacetic acid, polyphosphoric acid, etc. Lewis acids such as acid, zinc chloride, and solid acids are all used as catalysts. In the actual application of these traditional catalysts, there are often problems such as large dosage, strong corrosion to equipment, and generally low yield; secondly, most of the traditional methods Use irritating and volatile organic solvents, such as a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D209/08C07D209/94C07D209/88C07D495/04C07D209/80C07D209/60B01J31/02
Inventor 许丹倩吴健罗书平徐振元
Owner ZHEJIANG UNIV OF TECH
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