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Polysubstituted pyrrole compound and synthesis method thereof

A synthesis method and multi-substitution technology are applied in the field of pyrrole derivatives and synthesis thereof, and achieve the effects of cheap and easy-to-obtain raw materials, regulation of immunity, and low cost

Active Publication Date: 2020-02-04
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis of polysubstituted pyrimides using enaminones and α-diazo esters as starting materials has not been reported yet.

Method used

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  • Polysubstituted pyrrole compound and synthesis method thereof
  • Polysubstituted pyrrole compound and synthesis method thereof
  • Polysubstituted pyrrole compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Sequentially weigh 1-keto-1-phenyl-3-benzylamino-2-propene 2a (0.5mmol), tetraacetonitrile copper hexafluorophosphate (0.005mmol) in a 25mL Schlenk reaction flask, add 3mL of acetonitrile, at 40 Stir in an oil bath at ℃ for 2 minutes, add α-methyl diazophenylacetate 3a (0.6 mmol), and react for 20 hours. After the reaction, the mixture was cooled to room temperature, extracted with dichloromethane and water, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum Ether (60-90° C.) / ethyl acetate, v / v=50:1), the target product 1aa was obtained as a colorless oil (110 mg, yield 60%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0030]

[0031] Sequentially weigh 1-keto-1-phenyl-3-benzylamino-2-propene 2a (0.5mmol) and cuprous trifluoromethanesulfonate (0.1mmol) in a 25mL Schlenk reaction flask, add 2mL of DMF, and Stir in an oil bath at 60°C for 2 minutes, add ethyl α-diazophenylacetate 3b (0.7 mmol), and react for 10 hours. After the reaction, the mixture was cooled to room temperature, extracted with dichloromethane and water, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum Ether (60-90° C.) / ethyl acetate, v / v=50:1) to obtain the target product 1ab (105 mg, yield 55%) as a colorless oil. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0033]

[0034] Sequentially weigh 1-keto-1-phenyl-3-benzylamino-2-propene 2a (0.5mmol), copper acetate (0.1mmol) into a 25mL Schlenk reaction flask, add DCE 2mL, and place in an oil bath at 80°C Stir for 2 minutes, add α-ethyl diazoacetate 3c (2.5mmol), and react for 48 hours. After the reaction is over, the mixture is cooled to room temperature, extracted with dichloromethane and water, and the organic phase is collected, dried over anhydrous sodium sulfate, and filtered. The volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=50:1) to obtain the colorless oily target product 1ac ( 61 mg, yield 40%). The target product was confirmed by NMR and high-resolution mass spectrometry.

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Abstract

The invention discloses a polysubstituted pyrrole compound and a synthesis method thereof. Enaminone and alpha-diazo ester are adopted as starting materials, a copper salt is adopted as a catalyst, and under a heating condition, the polysubstituted pyrrole compound is prepared through a carbene insertion reaction and an aryl migration reaction. The method is novel and easy to obtain in raw materials, simple and convenient to operate, simple and mild in synthesis reaction conditions and wide in substrate universality.

Description

technical field [0001] The invention relates to pyrrole derivatives and a synthesis method thereof, in particular to a multi-substituted pyrrole compound and a synthesis method thereof. Background technique [0002] Pyrrole is an important class of compounds in drug research, and is an important skeleton structure of many natural products. As a structural unit, pyrrole is one of the foundations of biochemistry. Because of its special structure and electron-rich nature, it is prone to electrophilic attack, and because it contains nitrogen atoms, it can interact with many biomolecules through hydrogen bonds. These characteristics make it play an important role in natural medicine and artificial medicine, and have antiviral, antibacterial, antitumor, antihypercholesterolemia and other effects (Top.Heterocycl.Chem., 2006, 2, 53). The currently marketed multi-substituted azole drugs include the lipid-lowering drug atorvastatin, the non-steroidal analgesic and anti-inflammatory d...

Claims

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Application Information

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IPC IPC(8): C07D207/34A61P35/00A61P31/18A61P37/06A61K31/40
CPCC07D207/34A61P35/00A61P31/18A61P37/06
Inventor 黄和李明瑞黄菲于杨孙义明
Owner NANJING NORMAL UNIVERSITY
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