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Double indolyl derivative synthesizing process

A technology of an indole alkyl group and a synthesis method, which is applied in the field of preparation of heterocyclic compounds, can solve problems such as not seen, and achieve the effects of no reduction in activity, simple operation and high yield

Inactive Publication Date: 2007-08-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no relevant literature report on the reaction of using this as a catalyst to catalyze the synthesis of bisindole alkyl compounds.

Method used

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  • Double indolyl derivative synthesizing process

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Embodiment one: the synthesis of bis-indolylmethane

[0017] Take 1 mmol of formaldehyde and 2 mmol of indole in a mortar, add solid super acid SO 4 2- / TiO 2 Catalyst, the dosage is 50 mg, ground and reacted at 50°C for 0.5-1.5 hours, then washed with ethyl acetate, filtered, and the filtrate is concentrated to obtain a crude product, which is further purified to obtain bis-indolylmethane with higher purity.

Embodiment 2

[0018] Embodiment two: the synthesis of bisindolephenyl methane

[0019] Take 1 mmol of benzaldehyde and 2 mmol of indole in a reaction flask, add 60 mg of solid superacid SO 4 2- / TiO 2 , placed in a grinding oatmeal, ground evenly, heated to about 50°C under an infrared lamp, after 0.5 hours, TLC detected that the reaction was complete, washed with ethyl acetate, filtered, and the filtrate was concentrated in vacuum to obtain a crude product, which was further purified to obtain a higher Purity bisindolephenylmethane.

[0020]

Embodiment 3

[0021] Embodiment three: the synthesis of bis-indoxythiophene methane

[0022] Take 1 mmol of thiophene-2-carbaldehyde and 2 mmol of indole in a reaction flask, add 45 mg of solid superacid SO 4 2- / TiO 2 , placed in a grinding oatmeal, ground evenly, heated to about 50°C under an infrared lamp, after 1.5 hours, TLC detected that the reaction was complete, washed with ethyl acetate, filtered, and the filtrate was concentrated in vacuum to obtain a crude product, which was further purified to obtain a higher Purity bisindolephenylmethane.

[0023]

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Abstract

The present invention discloses the synthesis process of double indolylalkyl derivative. Aldehyde and indole are made to produce synthesis reaction, and the aldehyde is selected from C1-C10 aliphatic aldehyde and aromatic aldehyde. The present invention features that super solid acid SO42- / TiO2 is used as catalyst in the amount of 30-80 mg for each millimole of aldehyde, and that double indolylalkyl compound is prepared through grinding reaction for 0.5-5 hr and subsequent washing with solvent, filtering and filtrate concentration. The present invention adopts super solid acid to replace traditional protonic acid or Lewis acid, and no solvent in preparing double indolylalkyl compound, and has no environmental pollution caused by organic solvent, high reaction yield, short production period and simple operation.

Description

technical field [0001] The invention relates to the preparation of a heterocyclic compound containing a five-membered ring fused with other rings, and the heteroatom is a nitrogen atom, in particular to a method for synthesizing a bisindole alkyl compound. Background technique [0002] Indole compounds widely exist in nature, and many indole derivatives have certain physiological activities. Bis-indole alkyl compounds and their derivatives exist in the biologically active metabolites of continental and marine protozoa. These compounds have certain activities, such as: anti-tumor, anti-virus, anti-bacterial and anti-inflammatory and other physiological activities. Therefore, it has aroused great interest of organic chemists and pharmacologists. Among them, bis-indolylmethane has become a commercial product. [0003] The synthesis of bis-indole alkyl compounds was reported as early as the 19th century. Over the past 100 years, the synthesis of bis-indole alkyl compounds ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14C07D409/14
Inventor 纪顺俊曾晓飞
Owner SUZHOU UNIV
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