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Method for preparing pyrrole derivative

A technology of compounds and aromatic heterocycles, applied in the field of preparation of pyrrole derivatives, can solve the problems of difficult to obtain, unstable raw materials such as pyrrole and 3-pyrroline, and high price

Inactive Publication Date: 2012-11-14
EAST CHINA UNIV OF SCI & TECH
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Problems solved by technology

[0018] 1,4-bis-(dimethylamino)-1,3-butadiene, 1,4-dichloro-1,4-dimethoxybutane, 2-chlorocyclopropylformaldehyde, 3-hydroxyproline and 3-pyrroline pyrrole are expensive and difficult to obtain, raw materials such as pyrrole and 3-pyrroline are unstable and need to be reacted under inert conditions

Method used

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  • Method for preparing pyrrole derivative

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preparation example Construction

[0041] In the preparation method of the present invention, thin layer chromatography (TLC) can be used to judge the end point of the preparation reaction (petroleum ether / ethyl acetate=10:1 (v / v)); and the obtained formula I The crude product of the shown compound can be purified by existing conventional purification methods such as recrystallization or column chromatography (column chromatography adopts a silica gel column, and the eluent is petroleum ether / ethyl acetate=10:1 (v / v)) .

[0042] The method for preparing N-substituted pyrrole derivatives of the present invention has the advantages of wide source of raw materials, cheap and easy to obtain, simple and easy operation, no need for inert gas protection in the whole preparation process, high yield and the like.

Embodiment 1

[0045] Preparation of N-(4-nitrobenzyl)-1H-pyrrole:

[0046]

[0047] Suspend p-nitrobenzaldehyde (0.756g, 5mmol) and 4-hydroxy-L-proline (0.983g, 7.5mmol) in 10mL of redistilled N,N-dimethylformamide (DMF), Stirring and heating to reflux, reacting for about 30min, the reaction solution was cooled naturally, the solvent was evaporated under reduced pressure, and silica gel column chromatography (eluent was petroleum ether / ethyl acetate=10:1 (v / v)) gave N-(4 -Nitro-benzyl)-1H-pyrrole 0.88g, light yellow solid, yield: 87%; mp: 59.9~60.0℃;

[0048] 1 H NMR (400MHz, CDCl 3. )ppm 8.17 (2H, d, J = 8.67Hz), 7.20 (2H, d, J = 8.57Hz), 6.70 (2H, t, J = 1.97, 1.97Hz), 6.25 (2H, t, J = 1.99, 1.99Hz), 5.19(2H, s);

[0049] 13 C NMR (101MHz, CDCl 3 ) ppm 147.46, 145.76, 127.38, 124.02, 121.26, 109.41, 52.56;

[0050] MS, m / z(relative intensity): 202.1(100), 203.1(10.0), 201.1(28.5), 156.1(10.7), 155.1(7.2), 154.1(7.4), 136.0(23.5), 128.1(5.8), 127.1 (4.1), 106.0 (23.2), 90.0 (15....

Embodiment 2

[0052] Preparation of N-(4-nitrobenzyl)-1H-pyrrole:

[0053]

[0054] Suspend p-nitrobenzaldehyde (0.756g, 5mmol) and 4-hydroxyl-L-proline (0.983g, 7.5mmol) in 10mL[bmIm]BF 4 , stirred and heated to 150°C for 30 minutes, the reaction solution was cooled naturally, poured into water after the reaction solution was naturally cooled, extracted with ethyl acetate, dried over anhydrous sodium sulfate, the filtrate was evaporated under reduced pressure to remove the solvent, silica gel column chromatography (elution The solvent is petroleum ether / ethyl acetate=10:1 (v / v)) to obtain 0.81 g of a light yellow solid, and the yield is 80%. mp: 59.9~60.0℃;

[0055] 1 H NMR (400MHz, CDCl 3 )ppm 8.17 (2H, d, J = 8.67Hz), 7.20 (2H, d, J = 8.57Hz), 6.70 (2H, t, J = 1.97, 1.97Hz), 6.25 (2H, t, J = 1.99, 1.99Hz), 5.19(2H, s);

[0056] 13 C NMR (101MHz, CDCl 3. ) ppm 147.46, 145.76, 127.38, 124.02, 121.26, 109.41, 52.56;

[0057] MS, m / z(relative intensity): 202.1(100), 203.1(10.0), 2...

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Abstract

The invention relates to a method for preparing an N-substituted pyrrole derivative. The method comprises the step of carrying out a reaction on aromatic aldehyde and 4-hydroxy-L-proline in a reaction medium at the temperature of 80 DEG C-200 DEG C in the presence of an acidic catalyst so as to prepare a target product. The method for preparing the N-substituted pyrrole derivative has the advantages that a raw material is cheap and available, operation is simple and practicable, inert gas dose not need to be used for protection in the whole preparation process, yield is high, and the like.

Description

technical field [0001] The present invention relates to a method for preparing pyrrole derivatives, in particular to a method for preparing N-substituted pyrrole derivatives. Background technique [0002] Pyrrole derivatives have a variety of biological activities. Atorvastatin calcium, the active ingredient of Lipitor, a hypolipidemic drug currently used clinically, is a pyrrole derivative. In recent years, it has been found that N-(arylmethyl)pyrrole compounds have an inhibitory effect on HIV-1gp41 (J.Med.Chem.2008,51:7843-7854; Bioorg.Med.Chem.,2008,16:3039- 3048), some functional materials also contain such structures (J. Phys. Chem. 1991, 95: 1737-1742). Therefore, the research on the synthetic method of N-substituted pyrrole derivatives is of great significance. [0003] The Paal-Knoor method is a common method for preparing pyrrole derivatives by reacting primary amines with 1,4-dicarbonyl compounds. Improved Paal-Knoor method: N-(arylmethyl)pyrroles can be prepare...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/325C07D207/323C07D207/327C07D409/06C07D405/06
Inventor 虞心红邹志芹张曼曼邓泽军罗婷徐子安徐辉
Owner EAST CHINA UNIV OF SCI & TECH
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