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Preparation method of polysubstituted pyrrole derivative

A technology of pyrrole derivatives and multiple substitutions, applied in organic chemistry and other fields, can solve problems such as environmental pollution, high price, and high safety risks, and achieve the effects of reducing environmental pollution risks, reducing synthesis costs, and simplifying the process flow

Active Publication Date: 2018-08-24
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art has the following deficiencies: one is that the oxidizing agent used is large in amount and expensive, which greatly increases the production cost; High environmental pollution and safety risks

Method used

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  • Preparation method of polysubstituted pyrrole derivative
  • Preparation method of polysubstituted pyrrole derivative
  • Preparation method of polysubstituted pyrrole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] as attached figure 1 According to the technological process, take tetrahydropyrrole 5-(4-methoxyphenyl)-pyrrolidine-2,3,4-tricarboxylic acid methyl ester 70.3 mg (equivalent to 0.20 mmol), cuprous bromide 2.9 mg ( Equivalent to 0.02 mmol), 2,2,6,6-tetramethylpiperidine- N - 3.1 mg of oxygen free radicals (equivalent to 0.02 mmol) and 1.0 ml of 1,2-dichloroethane were added to the reaction vessel, and heated and stirred at 80 degrees Celsius for 5 hours under an oxygen atmosphere. plate) analysis until the reaction is complete. The mixture obtained above was poured into water, filtered, washed and dried to obtain a crude product. The crude product was separated by column chromatography to obtain 59.8 mg of the target polysubstituted pyrrole derivative of this example (86% yield).

[0026] The target product in Example 1 was analyzed by a nuclear magnetic resonance spectrometer (model: AVANCE 400MHz, manufacturer: Bruker, Switzerland) to obtain figure 2 The H NMR spe...

Embodiment 2

[0029] as attached figure 1 The technological process of taking tetrahydropyrrole 5-cyclohexyl-3-phenyl-pyrrolidine-4-formic acid methyl ester-2-formic acid ethyl ester 71.9 mg (equivalent to 0.20 mmol), tetraacetonitrile cuprous hexafluorophosphate 3.7 mg (equivalent to 0.01 mmol), 4-acetamido-2,2,6,6-tetramethylpiperidine- N - 4.3 mg of oxygen free radicals (equivalent to 0.02 mmol) and 0.8 ml of benzene were added to the reaction vessel, heated and stirred at 90 degrees Celsius for 3 hours under an oxygen atmosphere, and analyzed by thin layer chromatography (TLC spot plate) until the reaction was complete . The mixture obtained above was poured into water, filtered, washed and dried to obtain a crude product. The crude product was separated by column chromatography to obtain 53.3 mg (yield: 75%) of the target product of this example, the multi-substituted pyrrole derivative.

Embodiment 3

[0031] as attached figure 1 The technological process of tetrahydropyrrole 3-methyl-5-pentyl-pyrrolidine-2,4-dicarboxylate 71.9 mg (equivalent to 0.20 mmol), copper acetate 5.4 mg (equivalent to 0.03 mmol) , 4-carbonyl-2,2,6,6-tetramethylpiperidine- N - 5.1 mg of oxygen free radicals (equivalent to 0.03 mmol) and 0.6 ml of ethyl acetate were added to the reaction vessel, heated and stirred at 80 degrees Celsius for 4 hours under an oxygen atmosphere, and analyzed by thin layer chromatography (TLC spot plate), until The response is complete. The mixture obtained above was poured into water, filtered, washed and dried to obtain a crude product. The crude product was separated by column chromatography to obtain 42.2 mg of the multi-substituted pyrrole derivative, the target product of this example (yield: 79%)

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Abstract

The invention discloses a preparation method of a polysubstituted pyrrole derivative. By taking a copper salt as a catalyst, a free radical of nitroxide as a co-catalyst, and oxygen derived from air as a final oxidant, the polysubstituted pyrrole derivative is prepared from tetrahydropyrrole. In the process of the invention, only a catalytic amount of copper catalyst and a non-metal co-catalyst are used, and the used oxidant is low in price, the only by-product is water, the post-treatment process is simpler, and therefore the risk of environmental pollution is significantly reduced; the wholeprocess is carried out under an oxygen atmosphere, is not sensitive to moisture, and can be routinely operated under loose reaction conditions; related products can be produced for the fields of biology, pesticides and medicine, and the multi-substituted pyrrole derivative with abundant sources and low price is provided in an environment-friendly way.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of pyrrole derivatives, in particular to a preparation method of multi-substituted pyrrole derivatives. Background technique [0002] Pyrrole derivatives are widely used in the fields of biology, pesticides, medicine and organic semiconductor materials, and are intermediates in the production of drugs, dyes and organic semiconductor materials. For example: it is the key structural unit of porphyllinogen, heme and chlorophyll; in addition, it is the core structural unit of the antihypertensive and lipid-lowering drug atorvastatin and the analgesic and anti-inflammatory drug ketorolac; The key intermediate of base. In recent years, studies have confirmed that the biological activity of pyrrole derivatives has also played a positive role in anti-tumor, anti-bacterial, anti-virus, acaricidal, anti-inflammatory, anti-arrhythmic, anti-hypertensive and other aspect...

Claims

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Application Information

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IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 胡华友刘燕罗政卢明祝韦长梅
Owner HUAIYIN TEACHERS COLLEGE
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