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A New Green Synthesis of Di-Indolymethane(DIM) Derivatives
- Oct 16, 2019 -

Di-Indolymethane(DIM) has special physiological activity and is a good anticancer drug. A series of diindolyl alkanes were synthesized by the reaction of indole with aldehydes and ketones. The process conditions of solvent, temperature and reaction time were discussed. The optimum conditions were: water as solvent, temperature 30 ~ 40 ℃, reaction time 3 hours, under which the highest yield was 83%. The method is mild and simple, safe and environmental protection, and is a good synthesis method.

In recent years, due to its unique physiological activities, such as promoting the metabolism of estrogen in human body, regulating the hormone metabolites secreted by some cancer cells, diindomethane is a good anticancer drug, so its synthesis has been widely concerned. At present, some synthetic methods have been reported, such as the synthesis of diindomethane derivatives by using oxalic acid as catalyst, montmorillonite K10 ZnCl as catalyst, and the synthesis of diindomethane derivatives by grinding under the catalysis. All of these methods have some defects, such as expensive catalyst, non environmental protection of catalyst system, complex process conditions and so on. Therefore, it has become an important research direction to find efficient and cheap catalytic system and environmentally friendly synthesis method. In recent years, sulfamic acid has replaced conventional acid catalyst in many fields of organic synthesis due to its low cost, safety, convenient transportation and environmental friendliness. In this paper, diindolyl alkanes were synthesized by the reaction of indole with aldehydes or ketones in green solvent water under mild conditions using sulfamic acid as catalyst.


1. Main instruments and reagents

Instruments: al204 electronic balance, hdm-250 constant temperature magnetic electrothermal sleeve, wfh-203 three purpose ultraviolet analyzer, re-52aa rotary evaporation instrument, SHB-B95 circulating water multi-purpose vacuum pump, AgI lent lc-msd (ion trap VC) liquid mass spectrometer, jeolecx-500 superconducting nuclear magnetic resonance spectrometer.

Reagents: indonoise, sulfamic acid, benzaldehyde, cyclohexanone, 3-pentanone, acetaldehyde, all of the above reagents are commercially available analytical reagents.

2. Synthesis method

Add 236mg (2mmol) of Indy and 105mg of benzaldehyde to the round bottom flask.

(1mmol), sulfamic acid 97mg (1mmol), then add 10ml of water, stir at room temperature (18-25 ℃) for 6h, TLC followed up the reaction. Then the ethyl acetate was extracted, washed twice, dried and distilled under reduced pressure to remove the ethyl acetate. The purified product was obtained by elution chromatography with petroleum ether and ethyl acetate.

3. Conclusion

We have developed a new method for the synthesis of diindolmethane derivatives. This method uses cheap and environmentally friendly solid acid sulfamic acid as catalyst and reacts in green solvent water under mild conditions and simple operation. It can react with aldehydes and ketones with small steric hindrance to obtain high yield. It is a new method for the synthesis of diindolmethane derivatives that has not been reported.

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