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Preparation method for 3-sulfo-indoles compound

A technology for thioindole and compounds, which is applied in the field of preparation of 3-thioindole compounds, can solve problems such as complex process, lower performance of 3-thioindole compounds and product yield, and achieve substrate Wide adaptability, good industrial application prospects, and environmentally friendly effects

Inactive Publication Date: 2017-11-24
GANNAN NORMAL UNIV
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Problems solved by technology

Although great progress has been made in the research on the synthesis of 3-substituted indole compounds, the starting materials used in the synthesis process generally require multi-step synthesis, the process is complicated, and due to the use of expensive transition metals such as Palladium, vanadium, etc. are used as catalysts, and some metal elements will remain in the product during the reaction process and separation, and the introduction of metal ions will reduce the performance and product yield of 3-thioindole compounds

Method used

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  • Preparation method for 3-sulfo-indoles compound
  • Preparation method for 3-sulfo-indoles compound
  • Preparation method for 3-sulfo-indoles compound

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preparation example Construction

[0052] The invention provides a kind of preparation method of 3-thioindole compound, comprises the following steps:

[0053] Perform photocatalytic substitution reaction of thiophenolic compound and indole compound under the action of organic solvent and photocatalyst to obtain 3-thioindole compound;

[0054] The thiophenolic compound has the structure shown in formula I:

[0055]

[0056] The indole compound has a structure shown in formula II:

[0057]

[0058] The 3-thioindole compound has the structure shown in formula III:

[0059]

[0060] R in the formula I 1 is methoxy-substituted phenyl, alkyl-substituted phenyl or halogen-substituted phenyl;

[0061] R in the formula II 2 is hydrogen, alkyl, halogen, methoxy, nitro, nitrile, hydroxymethyl, aminomethyl or trifluoromethyl;

[0062] R 3 is hydrogen, alkyl, aminomethyl, aminoethyl, formyl or N,N-dimethyl;

[0063] R 4 is hydrogen, alkyl, aminomethyl, hydroxymethyl, phenyl or tolyl;

[0064]The photocata...

Embodiment 1

[0092] Add 0.1mmol 1-methylindole, 0.2mmol p-methoxythiophenol, 0.02mmol Rose Bengal, 0.1ml dichloromethane into the reaction flask, and stir the reaction at 22°C under the irradiation of 400nm light source for 20 Hours, after the reaction was completed, it was separated and purified by column chromatography. The volume ratio of petroleum ether and ethyl acetate in the column chromatography eluent was 24:1, and the purified target product was obtained with a yield of 64%. The structural characterization data of the resulting product are as follows:

[0093] 1 H NMR (400MHz, CDCl 3 ): δ=7.62(d, J=8.0Hz, 1H), δ=7.35(d, J=8.0Hz, 1H), δ=7.29(d, J=8.0Hz, 1H), δ=7.24(d, J=8.0Hz, 1H), δ=7.17-7.10(m, 3H), δ=6.71-6.71(m, 2H), δ=3.81(s, 3H), δ=3.71(s, 3H);

[0094] 13 C NMR (100MHz, CDCl 3 )δ=157.7, 137.5, 134.5, 128.4, 119.7, 114.5, 109.7, 102.3, 55.3, 33.1;

[0095] MS (EI, 70eV): m / z (%) = 269 (M+), 254, 237, 222, 210, 162, 135, 120, 102 (100).

[0096] The structural characte...

Embodiment 2

[0100] Add 0.2mmol of 1-methylindole, 0.3mmol of p-fluorothiophenol, 0.002mmol of red Y, 0.2ml of dichloromethane into the reaction bottle, under the irradiation of 350nm light source, stir and react at 26°C for 6 hours, the reaction After completion, separation and purification by column chromatography, the volume ratio of petroleum ether and ethyl acetate in the eluent of column chromatography was 8:1, and the purified target product was obtained with a yield of 30%.

[0101] The structural characterization data of the resulting product are as follows:

[0102] 1 H NMR (400MHz, CDCl 3 ): δ=7.58(d, J=8Hz, 1H), δ=7.36(d, J=8Hz, 1H), δ=7.30-7.26(m, 2H), δ=7.17-7.14(m, 1H), δ=7.08-7.05(m,2H), δ=6.86-6.82(m,2H), δ=3.80(s,3H);

[0103] 13 C NMR (100MHz, CDCl 3 )δ=162.1, 159.7, 137.6, 134.9, 134.5, 129.6, 127.8, 127.7, 122.7, 120.6, 119.6, 115.8, 115.6, 109.8, 101.4, 33.1;

[0104] MS (EI, 70eV): m / z (%) = 257 (M+), 242, 225, 183, 162, 121 (100).

[0105] According to the ab...

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Abstract

The invention relates to the technical field of organic synthesis and provides a preparation method for a 3-sulfo-indoles compound. The 3-sulfo-indoles compound is acquired through the substitution reaction of thiophenols compound and indoles compound under the photo-catalytic effect of photo-catalyst and organic solvent, wherein the photo-catalyst comprises one or more of eosin B, eosin Y and rose bengal. According to the preparation method provided by the invention, the reaction condition is mild, no alkali or oxidizing agent is required, no transition metal catalyst participates into the reaction, the adverse effect of the metal residue to the product performance is effectively avoided, the product performance is promoted, the product yield is increased to 70%, the multi-step synthesis of the reaction raw materials is not required and the technological process is simplified.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-thioindole compounds. Background technique [0002] 3-Substituted indole widely exists in various natural products, and has attracted widespread attention due to its good biological activity. Among them, the 3-thioindole structure is the basic structural unit of many natural products, bioactive molecules and drug molecules, and these compounds have a variety of physiological activities, such as anticancer activity, anti-HIV activity, antibacterial activity, anti-obesity and Inhibits tubulin polymerization and inhibits the growth of breast cancer cells, among others. [0003] In recent years, those skilled in the art have developed some effective methods for building 3-thioindole compounds, specifically transition metal-catalyzed reactions such as palladium and vanadium (Nishimura.T.; Uemura.S.J.Org.Chem.2004, 69, 7688-7693; Zhu.D.; Gu.Y.J.Am....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 郭维谭雯郑绿茵赵明明陶开亮范小林
Owner GANNAN NORMAL UNIV
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