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2-cyanopyrrole compound and synthesis method thereof

A cyanopyrrole and compound technology, which is applied in the field of 2-cyanopyrrole compounds and their synthesis, can solve the problems of difficult source of raw material substrates, expensive raw material preparation, harsh reaction conditions, etc., and achieves good substrate adaptability and raw material Easy-to-obtain, easy-to-use effects

Active Publication Date: 2020-03-24
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] In summary, there are mainly the above methods for the synthesis of 2-cyanopyrrole compounds at present, but the source of some raw materials and substrates in the above methods is not easy and relatively complicated, and it often needs to be obtained through several steps of reaction, and the preparation of raw materials is relatively expensive; or The reaction conditions are relatively harsh, it is not easy to popularize, and the reaction cost is relatively high

Method used

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  • 2-cyanopyrrole compound and synthesis method thereof
  • 2-cyanopyrrole compound and synthesis method thereof
  • 2-cyanopyrrole compound and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrolyl]-4-methylbenzenesulfonamide

[0036] N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrole]-4-methylbenzenesulfonamide adopts the following steps: ① Add 136 mg of 2,3-di Chloro-4,5-dicyano-p-benzoquinone (0.6 mmol), 86 mg of 4-methyl-N-[(2E)-3-phenyl-2-propene]benzenesulfonamide (0.3 mmol), under nitrogen Under atmosphere, 1.5 mL of chlorobenzene, 3 μL of trifluoromethanesulfonic acid (0.03 mmol), and 75 mg of tert-butylisonitrile (0.9 mmol) were added, and heated to 80-90°C. The reaction was tracked by thin-layer chromatography until the raw materials disappeared (3h); ② After the reaction, the product was extracted with ethyl acetate, washed with saturated brine, and dried with a rotary evaporator to remove the solvent to obtain a crude product; ③ The crude product obtained is directly separated and purified by column chromatography (petroleum ether: ethyl acetate=8:1), to obtain 83 mg of N-[1-(tert-butyl)-2-cyano-5-p...

Embodiment 2

[0042] Example 2: N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrolyl]-N-methyl-4-methylbenzenesulfonamide

[0043] N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrole]-N-allyl-4-methylbenzenesulfonamide adopts the following steps: ①Add 136mg to a 15mL test tube 2,3-dichloro-4,5-dicyano-p-benzoquinone (0.6mmol), 90mg of 4-methyl-N-[(2E)-3-phenyl-2-propene]-N-methyl Benzenesulfonamide (0.3mmol), under a nitrogen atmosphere, add 1.5mL of chlorobenzene, 3μL of trifluoromethanesulfonic acid (0.03mmol), 75mg of tert-butylisonitrile (0.9mmol), and heat to 80-90°C. The reaction was tracked by thin-layer chromatography until the raw materials disappeared (3h); ② After the reaction, the product was extracted with ethyl acetate, washed with saturated brine, and dried with a rotary evaporator to remove the solvent to obtain a crude product; ③ The crude product obtained is directly separated and purified by column chromatography (petroleum ether: ethyl acetate=10:1), to obtain 73 mg of N-[1-(tert-b...

Embodiment 3

[0049] Example 3: N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrolyl]-N-cyclohexyl-4-methylbenzenesulfonamide

[0050] N-[1-(tert-butyl)-2-cyano-5-phenyl-1H-pyrrolyl]-N-cyclohexyl-4-methylbenzenesulfonamide adopts the following steps: ①Add 136mg 2,3-dichloro-4,5-dicyano-p-benzoquinone (0.6mmol), 111mg of 4-methyl-N-[(2E)-3-phenyl-2-propene]-N-ring Hexylbenzenesulfonamide (0.3mmol), under nitrogen atmosphere, add 1.5mL of chlorobenzene, 3μL of trifluoromethanesulfonic acid (0.03mmol), 75mg of tert-butylisonitrile (0.9mmol), and heat to 80-90°C. The reaction was tracked by thin-layer chromatography until the raw materials disappeared (3h); ② After the reaction, the product was extracted with ethyl acetate, washed with saturated brine, and dried with a rotary evaporator to remove the solvent to obtain a crude product; ③ The crude product obtained is directly separated and purified by column chromatography (petroleum ether: ethyl acetate=10:1) to obtain 71 mg of N-[1-(tert-butyl)-2-c...

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Abstract

The invention relates to a 2-cyanopyrrole compound and a synthesis method thereof. The structural formula of the compound is shown in the specification, wherein R1 is hydrogen, fluorine, chlorine, methoxyl and tert-butyl; R2 is hydrogen or chlorine; R3 is hydrogen, methyl, cyclohexyl, phenyl or allyl. The 2-cyanopyrrole compound disclosed by the invention is a very valuable organic synthesis intermediate, can be converted into other corresponding active compounds, and shows various reaction activities. According to the method, the used raw materials are simple and easy to obtain, tert-butyl isocyanide is used as a cyano source of the reaction, and the 2-cyanopyrrole compound is obtained under the catalysis of trifluoromethanesulfonic acid. The reaction has good reaction activity and substrate adaptability. And a conventional reaction solvent is used in the reaction process, so that the method is simple to operate, mild in condition, environment-friendly and medium in yield, and has a good development prospect in industrial production.

Description

technical field [0001] The present invention relates to a kind of 2-cyanopyrrole compound and its synthetic method Background technique [0002] The pyrrole ring skeleton is an important skeleton of many natural products, biomolecules and drug molecules, and is also an intermediate of many drug molecules. It is widely used in the field of medicinal chemistry because of its good biological activity. For example: Artico et al. extracted HDAC inhibitors containing pyrrole rings from Streptomyces hygroscopicus (see references: Artico, M. et al. J. Med. Chem., 1990, 33, 2845). Di Santo R and others synthesized a variety of compounds with antibacterial properties and measured their activity and conducted QSAR studies. The results showed that the derivatization of 1-aryl-1-(1-methyl-4-arylpyrrolyl) imidazole All compounds showed relatively high inhibitory activity (see reference: Di Santo, R. et al. J. Med. Chem., 2005, 48, 5140). Wilkerson et al found that selective cyclooxygena...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 刘秉新张亚萍许斌谭启涛丁昌华
Owner SHANGHAI UNIV