Method for preparing N-(3'-aryl allyl)pyrrole derivatives

A technology of phenyl and compound, applied in the field of preparation of N-pyrrole derivatives, can solve the problems of harsh reaction conditions, high price, instability and the like, and achieves the effects of high yield, simple and easy operation, and wide source of raw materials

Inactive Publication Date: 2011-11-23
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0007] The 3-pyrroline used in the above method, Wittig reagent and pyrrole etc. are expensive and difficult to obtain, and unstable, harsh reaction conditions

Method used

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  • Method for preparing N-(3'-aryl allyl)pyrrole derivatives
  • Method for preparing N-(3'-aryl allyl)pyrrole derivatives
  • Method for preparing N-(3'-aryl allyl)pyrrole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of N-(3-phenylallyl)pyrrole:

[0033]

[0034] Cinnamaldehyde (0.66g, 0.63ml, 5mmol) and 4-acetoxy-L-proline (1.37g, 7.5mmol) were suspended in 10mL of redistilled N,N-dimethylformamide (DMF) , stirred and heated to 125 ° C for 4 h, the reaction solution was naturally cooled, the solvent was evaporated under reduced pressure, and silica gel column chromatography (eluent was petroleum ether / ethyl acetate = 10:1 (v / v)) to obtain N-benzene Pronyl-1H-pyrrole 0.65g, yellow liquid, yield: 71%;

[0035] 1 H NMR (400MHz, CDCl3) ppm 7.27 (5H, m), 6.68 (2H, s), 6.44 (1H, d, J=15.83Hz), 6.28 (1H, td, J=15.77, 6.10, 6.10Hz), 6.18(2H, s), 4.58(2H, d, J=6.00Hz);

[0036] 13 C NMR (101MHz, CDCl3) ppm 136.34, 132.60, 128.67, 127.96, 126.58, 125.57, 120.70, 108.49, 51.62;

[0037] MS, m / z(relative intensity): 183.1(69.1), 117.1(100), 184.1(7.44), 182.1(4.8), 143.1(2.6), 128.1(2.6), 118.1(7.9), 116.1(6.9), 115.1 (37.3).

Embodiment 2

[0039] Preparation of N-(3-phenylallyl)pyrrole:

[0040]

[0041] Except that the amount of 4-acetoxy-L-proline is changed from (1.37g, 7.5mmol) to (0.913g, 5mmol), other is the same as in Example 1, silica gel column chromatography (eluent is sherwood oil / Ethyl acetate=10:1 (v / v)) separated by silica gel column chromatography to obtain 0.50 g of N-phenylpropenyl-1H-pyrrole, yellow liquid, yield: 54.6%;

[0042] 1 H NMR (400MHz, CDCl3) ppm 7.27 (5H, m), 6.68 (2H, s), 6.44 (1H, d, J=15.83Hz), 6.28 (1H, td, J=15.77, 6.10, 6.10Hz), 6.18(2H, s), 4.58(2H, d, J=6.00Hz);

[0043] 13 C NMR (101MHz, CDCl3) ppm 136.34, 132.60, 128.67, 127.96, 126.58, 125.57, 120.70, 108.49, 51.62;

[0044] MS, m / z(relative intensity): 183.1(69.1), 117.1(100), 184.1(7.44), 182.1(4.8), 143.1(2.6), 128.1(2.6), 118.1(7.9), 116.1(6.9), 115.1 (37.3).

Embodiment 3

[0046] Preparation of N-(3-phenylallyl)pyrrole:

[0047]

[0048] Cinnamaldehyde (0.66g, 0.63ml, 5mmol) and 4-acetoxy-L-proline (1.37g, 7.5mmol) were suspended in 10mL[bmIm]BF 4 , stirred and heated to 125°C for 12 hours, 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 to remove the solvent under reduced pressure, silica gel column chromatography (elution The agent is petroleum ether / ethyl acetate=10:1 (v / v)) to obtain N-phenylpropenyl-1H-pyrrole 0.58g, yellow liquid, yield: 63.4%;

[0049] 1 H NMR (400MHz, CDCl3) ppm 7.27 (5H, m), 6.68 (2H, s), 6.44 (1H, d, J=15.83Hz), 6.28 (1H, td, J=15.77, 6.10, 6.10Hz), 6.18(2H, s), 4.58(2H, d, J=6.00Hz);

[0050] 13 C NMR (101MHz, CDCl3) ppm 136.34, 132.60, 128.67, 127.96, 126.58, 125.57, 120.70, 108.49, 51.62;

[0051] MS, m / z(relative intensity): 183.1(69.1), 117.1(100), 184...

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Abstract

The invention relates to a method for preparing N-(3'-aryl allyl)pyrrole derivatives, which mainly comprises the following step of: reacting 3-aromatic (cycle) propenal with 4-acetoxyl-L-proline at the temperature of between 100 and 180DEG C (performing decarboxylation, redox amination and acetic acid removing aromatization) in an organic solvent such as N,N-dimethylformamide or ionic liquid such as 1-butyl-3-methylimidazolium tetrafluoroborate to obtain target objects. The method has the advantages of cheap and readily available raw materials, simple and practicable operation, high yield and the like.

Description

technical field [0001] The present invention relates to a kind of preparation method of N-substituted pyrrole derivative, specifically, relate to a kind of preparation method of N-(3'-aryl allyl) pyrrole derivative. Background technique [0002] Pyrrole is a common pharmacophore, and many drugs and natural product molecules contain pyrrole structures. N-(3'-arylallyl)pyrrole derivatives are important intermediates, and the study of their synthetic methods is of great significance. [0003] Literature adopts 3-pyrroline and cinnamaldehyde under the catalysis of benzoic acid in toluene reflux reaction 6h, N-alkylation-aromatization obtains N-(3'-phenylallyl) pyrrole, yield 50% (J .Am.Chem.Soc.2009, 131:16626-16627): [0004] [0005] Or use the Wittig reaction to obtain N-(3'-phenylallyl)pyrrole from the Wittig reagent, benzaldehyde and pyrrole under the action of sodium hydride, with a yield of 51% (Heterocycles, 1983, 20 (9), 1737-40; J. Org. Chem, 1966, 31(2), 467-471...

Claims

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Application Information

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IPC IPC(8): C07D295/03C07D295/073
Inventor 虞心红段绍亮邹志芹罗婷邓泽军马红梅
Owner EAST CHINA UNIV OF SCI & TECH
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