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Preparation method of N-dithiocarbamate indole compound

A technology of dithiocarbamic acid and compounds, applied in the direction of organic chemistry, to achieve the effects of high yield, mild reaction conditions and short reaction time

Active Publication Date: 2019-02-26
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there are few reports on the introduction of dithiocarbamate groups on heterocyclic rings, and there are few reports on the synthesis of dithiocarbamate indole.

Method used

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  • Preparation method of N-dithiocarbamate indole compound
  • Preparation method of N-dithiocarbamate indole compound
  • Preparation method of N-dithiocarbamate indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Indole (0.2mmol), N,N,N',N'-tetramethylthiuram (0.22mmol), potassium tert-butoxide (0.4mmol) and DCE (2.0mL) were added to a 5mL reaction flask respectively, Stir at room temperature. TLC tracking detection reaction. After 1 hour, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (17% ethyl acetate petroleum ether solution), obtain product 43.9mg, yield rate is 93%, reaction process is shown in the following formula:

[0027]

[0028] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0029] 1 H NMR (500MHz, CDCl 3 )δ7.65(d, Jδ7.69(d, J=7.7Hz), 7.40(dt, J=17.7, 9.2Hz), 7.27(dd, J=13.1, 5.6Hz), 7.17(d, J=3.1 Hz), 6.79(d, J=3.0Hz), 5.51–4.77(m).=7.7Hz, 1H), 7.45(d, J=8.1Hz, 1...

Embodiment 2

[0037] Add indole (0.2mmol), N,N,N',N'-tetramethylthiuram (0.22mmol), potassium tert-butoxide (0.4mmol) and toluene (2.0mL) respectively into a 5mL reaction flask, Stir at room temperature. TLC tracking detection reaction. After 1 hour, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (17% ethyl acetate petroleum ether solution), obtain product 37.3mg, productive rate is 79%, and reaction process is shown in the following formula:

[0038]

[0039] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0040] 1H NMR (500MHz, CDCl 3 )δ7.65(d, Jδ7.69(d, J=7.7Hz), 7.40(dt, J=17.7, 9.2Hz), 7.27(dd, J=13.1, 5.6Hz), 7.17(d, J=3.1 Hz), 6.79(d, J=3.0Hz), 5.51–4.77(m).=7.7Hz, 1H), 7.45(d, J=8...

Embodiment 3

[0042] Indole (0.2mmol), N,N,N',N'-tetramethylthiuram (0.22mmol), potassium tert-butoxide (0.4mmol) and 1,4-dioxo Hexacyclic (2.0 mL), stirred at room temperature. TLC tracking detection reaction. After 2 hours, starting material remained, but no more product. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (17% ethyl acetate petroleum ether solution), obtain product 25.0mg, productive rate is 53%, and reaction process is shown in the following formula:

[0043]

[0044] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0045] 1 H NMR (500MHz, CDCl 3 )δ7.65(d, Jδ7.69(d, J=7.7Hz), 7.40(dt, J=17.7, 9.2Hz), 7.27(dd, J=13.1, 5.6Hz), 7.17(d, J=3.1 Hz), 6.79(d, J=3.0Hz), 5.51–4.77(m).=7.7Hz, 1H), 7.45(d, J=8....

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Abstract

The invention discloses a preparation method of an N-dithiocarbamate indole compound. The preparation method of the N-dithiocarbamate indole compound comprises the step of using potassium tert-butoxide as alkali and an indole compound and a thiuram compound as a substrate to synthesize the N-dithiocarbamate indole compound in DCE or a methylbenzene solvent. According to the preparation method of the N-dithiocarbamate indole compound, the N-dithiocarbamate indole compound is synthesized for the first time by chemically and selectively forming an N-S bond. The preparation method of the N-dithiocarbamate indole compound, disclosed by the invention, has the advantages that reaction raw materials are cheap and easy to obtain; the preparation method is simple; by using the potassium tert-butoxide as the alkali to perform a reaction at room temperature, the reaction time is short, the yield is high and the operation is simple; and the method is suitable for synthesis of different types of N-dithiocarbamate indole compounds. The preparation method of the N-dithiocarbamate indole compound can be used for synthesizing a series of N-dithiocarbamate indole compounds, the synthesized product can be used as an intermediate compound for further constructing complex active compounds; and meanwhile, the compound has great drug activity potential.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing N-dithiocarbamate indole compounds at room temperature promoted by potassium tert-butoxide. Background technique [0002] Thioindole is a very important class of indole compounds, which are widely distributed in natural products and pharmaceutical active molecules as the core skeleton, so the synthesis of this type of compounds has been extensively studied. The reported methods for synthesizing thioindole compounds are mostly the reaction of introducing thioether at the 3-position of indole carbon, usually using disulfide or thiol as the sulfur source. Dithiocarbamate exists in many types of biologically active molecules, and the pharmaceutical activity of compounds containing dithiocarbamate structures has received continuous attention and research since the 20th century. Many kinds of heterocyclic compounds containing dithiocarbamate have bee...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07D401/12
CPCC07D209/08C07D401/12
Inventor 宋增强周岩谢自新张文歆梁广
Owner WENZHOU MEDICAL UNIV
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