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Study on The Synthesis of Di-indolymethane(DIM)
- Sep 27, 2019 -

Indole compounds not only exist widely in nature, but also have many physiological activities. The synthesis of natural products or derivatives with physiological activity from indole nuclei for screening activity has been the core of indole chemistry. Therefore, their research is very extensive and in-depth, especially how to synthesize indole derivatives more efficiently and green has attracted great attention. Among all kinds of indole derivatives, 3-substituted indoles are an important framework in the total synthesis of natural products and the design of drug molecular targets. Therefore, it is of great significance to study the 3-position substituted indole derivatives. On the basis of reviewing the progress in the regioselective Friedel-Crafts alkylation of indole ring at three sites, the Michael addition reaction of indole and a, beta-unsaturated carboxylic compounds catalyzed by palladium and the new method of preparing indole methane catalyzed by aminosulfonic acid were studied. These methods are simple in operation, mild in reaction conditions, environmentally friendly, regioselective and specific, and yields are good.


The main research contents and results are as follows:

1. A PdC12 (CHCN) was developed. / [bmim] [BF.] Catalyst system can effectively catalyze Michael addition of various indoles and different a, beta-unsaturated monkey-based compounds. Various factors affecting the reaction of indole Michael addition were studied. It was found that the solvent effect was very obvious, using ionic liquids [bmim] [BF]

It is much better than the catalytic effect of molecular solvents. The optimum reaction conditions were determined to be 2%.

PdC12 (CHACN) 2/[bmim][BF] catalytic system, reaction time is generally 2 hours, reaction temperature is 100 C. Using this optimum condition, 34 kinds of beta-indole-3-ketones were obtained in high yield, and a typical product 3b of Michael reaction was cultured in single crystal. The crystal structure of the compound was determined by X-ray diffraction analysis.

2. PdCl(CHaCN)a/[bmim][BF,] catalytic system promotes the Michael reaction of indole and a. Although the Michael reaction of beta-unsaturated ketone compound can be recycled for more than three times, its catalytic activity decreases gradually. Therefore, the mechanism of the reaction was further studied in this paper. The results show that although PdC12 (CH, CN) 2 is always understood as a Lewis acid catalyst for various addition reactions, we can distinguish between protonic acid and Lewis acid by HNMR analysis and 4-methyl-2, 6-di-tert-butylpyridine intervention experiments. Finally, we confirm that PdC1: (CH4CN) is a good catalyst for the synthesis of Lewis acid.

In [bmim] [BF,] some of the hydrolysis occurs to produce protons, and then protons as real active catalysts promote the Michael addition reaction of indole and a, beta-unsaturated ketones.

3. A new method for synthesis of diindolemethane from indole and aldehyde (ketone) catalyzed by solid strong acid monoaminosulfonic acid was developed. Various factors affecting the electrophilic substitution reaction were studied. It is found that the solvent effect is very obvious. The catalytic effect of alcohol solvents such as methanol and ethanol is much better than that of non-proton organic solvents such as ethyl ester, dichloromethane, toluene, anhydrous ether, benzene and tetrahydrofuran. The optimum reaction conditions were determined as follows: the dosage of catalyst sulfamic acid was 50%, the reaction solvent was methanol or ethanol, stirring reaction at room temperature for 1-6 hours. Using this optimum condition, 35 kinds of diindolemethane derivatives were obtained in high yield, and a typical product 5g was cultured in single crystal. The crystal structure of the compound was determined by X-ray diffraction analysis. Finally, we studied the recycling and recycling experiments of aminosulfonic acid, and found that aminosulfonic acid not only has high recovery rate, but also can be recycled, and its catalytic activity will not be reduced. Therefore, using inexpensive and recyclable aminosulfonic acid as catalyst, we have achieved a mild, efficient, green and inexpensive new synthesis method of indolemethane.

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