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Method for preparing dihydro pyrrole derivates

A technology of dihydropyrrole and derivatives, applied in the direction of organic chemistry and the like, can solve the problems of unsuitability for industrialization, inconvenient operation, and difficult to obtain raw materials, and achieves the effects of high reaction yield and safe and simple operation.

Inactive Publication Date: 2009-05-06
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has problems such as regioselectivity and low yield, and the raw material is not easy to obtain, so it needs to be prepared separately
One of the raw material preparation methods is to obtain the raw material in two steps, but in this method, a strong acidic and corrosive reagent perchloric acid is used, and it needs to be reacted at high temperature, so there is a great risk of explosion, which is very unfavorable for operation and industrialization (Angew.Chem., Int.Ed.1964, 3, 135); the second method uses imines, acid chlorides and highly toxic gas carbon monoxide as raw materials, and obtains the raw materials under palladium catalysis. Obviously, this method uses The highly toxic gas carbon monoxide brings great inconvenience to the operation and is also not suitable for industrialization (J.Am.Chem.Soc.2003, 125, 1474)

Method used

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  • Method for preparing dihydro pyrrole derivates
  • Method for preparing dihydro pyrrole derivates
  • Method for preparing dihydro pyrrole derivates

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Dissolve (E)-2-oxo-4-p-chlorophenyl-3-butenoic acid methyl ester (1mmol), aniline (1.2mmol) and rhodium acetate (0.01mmol) in toluene (6mL) to form a reaction system , Methyl phenyldiazoacetate (1.2 mmol) was dissolved in 3 mL of toluene to form a solution, and this solution was slowly added dropwise to the reaction system within 1 hour at 45°C. After the dropwise addition, the reaction solution was cooled to room temperature, 10 mL of toluene and citric acid monohydrate (0.2 mmol) were added, and the reaction mixture was refluxed with water for 4 hours through a water separator, the reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure , the crude product was obtained, and the crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:70~1:40) to obtain the corresponding dihydropyrrole derivative with a yield of 75%.

Embodiment 2

[0032] Dissolve (E)-2-oxo-4-m-bromophenyl-3-butenoic acid methyl ester (1mmol), aniline (1.2mmol) and rhodium acetate (0.01mmol) in toluene (6mL) to form a reaction system , methyl phenyldiazoacetate (1.2 mmol) was dissolved in 3 mL of toluene to form a solution, and this solution was slowly added dropwise to the reaction system within 1 hour at 45°C. After the dropwise addition, the reaction solution was cooled to room temperature, 10 mL of toluene and citric acid monohydrate (0.2 mmol) were added, and the reaction mixture was refluxed with water for 3 hours through a water separator, the reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure , to obtain a crude product, and the crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:70~1:40) to obtain the corresponding dihydropyrrole derivative with a yield of 70%.

Embodiment 3

[0034] Dissolve (E)-2-oxo-4-p-nitrophenyl-3-butenoic acid methyl ester (1mmol), aniline (1.2mmol) and rhodium acetate (0.01mmol) in toluene (6mL) to form a reaction system, methyl phenyldiazoacetate (1.2 mmol) was dissolved in 3 mL of toluene to form a solution, and this solution was slowly added dropwise to the reaction system within 1 hour at 45°C. After the dropwise addition, the reaction solution was cooled to room temperature, 10 mL of toluene and citric acid monohydrate (0.2 mmol) were added, and the reaction mixture was refluxed with water for 3 hours through a water separator, the reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure , the crude product was obtained, and the crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:70~1:20) to obtain the corresponding dihydropyrrole derivative with a yield of 84%.

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Abstract

The invention discloses a method for preparing a pyrrolin derivative, and relates to a method for preparing the pyrrolin derivative by a one-pot process. The method comprises the following steps: taking beta, gamma-unsaturated-alpha-keto ester, amine, diazo compound, metallic Lewis acid catalyst and organic acid catalyst according to a molar ratio of 1 to 1.2 to 1.2 to 0.01 to 0.2; dissolving the amine, the beta, gamma-unsaturated-alpha-keto ester and the metallic Lewis acid catalyst in organic solvent together to form a reaction system, and dissolving the diazo compound in the organic solvent within 1 hour to form solution, dripping the solution into the reaction system, catalyzing the diazo compound by metallic Lewis acid to decompose and form metallic carbine through three-component cascade reaction, making amine ylide formed by the metallic carbine and amine in situ trapped by the beta, gamma-unsaturated-alpha-keto ester in a 1, 4-addition mode; and then carrying out water by a water segregator to obtain the corresponding pyrrolin derivative. The method has the advantages of high atom economy, high efficiency, high yield, and so on, and the operation is safe and simple. The pyrrolin derivative is widely applied in the field of medicine chemical engineering.

Description

technical field [0001] The invention discloses a preparation method of dihydropyrrole derivatives, relates to a one-pot method for preparing dihydropyrrole derivatives, and belongs to the technical field of synthetic medicine and chemical industry. Background technique [0002] Dihydropyrrole derivatives are an important skeleton structure for building natural products and synthetic drugs. These compounds can be easily reduced to corresponding tetrahydropyrrole derivatives or generated through aromatization, and dihydropyrrole Derivatives act as key intermediates in the total synthesis of many natural products (J. Am. Chem. Soc. 2005, 127, 5342; J. Am. Chem. Soc. 2002, 124, 8584). In particular, dihydropyrrole derivatives containing multiple chiral centers and ortho-positions containing two or more aromatic groups have obvious biological activity (Tetrahedron 2006, 62, 7213), but the preparation methods for this type of compound are very unclear. Less (Tetrahedron 1990, 46,...

Claims

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Application Information

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IPC IPC(8): C07D207/277C07D207/16
Inventor 胡文浩朱映光翟昌伟岳永力杨琍苹
Owner EAST CHINA NORMAL UNIV
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