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Preparation method of polysubstituted pyrroline compound

A technology for dihydropyrroles and compounds is applied in the field of preparation of polysubstituted dihydropyrroles, which can solve complex problems and achieve the effect of mild reaction conditions.

Active Publication Date: 2020-08-28
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It can be seen that although there are many synthetic methods for multi-substituted dihydropyrrole derivatives, there are few reports on synthetic methods catalyzed by cheap metal iron and without acid and base participation, and most of the existing methods require complex iron catalysts

Method used

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  • Preparation method of polysubstituted pyrroline compound
  • Preparation method of polysubstituted pyrroline compound
  • Preparation method of polysubstituted pyrroline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] R is the preparation method of 1-p-toluenesulfonyl-3-benzoyl-4,4-dimethyl-dihydropyrrole with hydrogen:

[0036] (1) In a 10mL dry reaction tube, add raw materials N-2-methylallyl-N-3-phenylpropargyl p-toluenesulfonamide (0.170g, 0.5mmol), Fe (acac) 3 (0.1mmol), tert-butyl nitrite (0.103g, 1mmol), polymethylsiloxane (0.333g, 1.5mmol) and 10mL tetrahydrofuran, and the mixed system was reacted at 60°C for 24 hours. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure to obtain a crude product.

[0037] (2) Next, the crude product was dissolved in 10 mL of acetonitrile-water (9:1 by volume) solution, and a catalytic amount of iodine (12 mg) and hydrogen peroxide (1 mmol) were added, and reacted at room temperature for ...

Embodiment 2

[0040] Wherein R is the preparation method of 1-p-toluenesulfonyl-3-(4-methoxybenzoyl)-4,4-dimethyl-dihydropyrrole of 4-methoxyl group:

[0041] (1) In a 10mL dry reaction tube, add the raw material N-2-methylallyl-N-3-(4-methoxyphenyl)propargyl p-toluenesulfonamide (0.185 g, 0.5mmol), Fe(acac) 3 (0.1mmol), tert-butyl nitrite (0.103g, 1mmol), polymethylsiloxane (0.333g, 1.5mmol) and 10mL tetrahydrofuran, and the mixed system was reacted at 60°C for 24 hours. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure to obtain a crude product.

[0042] (2) Next, the crude product was dissolved in 10 mL of acetonitrile-water (9:1 by volume) solution, and a catalytic amount of iodine (12 mg) and hydrogen peroxide (1 mmol) were adde...

Embodiment 3

[0046] The preparation method of 1-p-toluenesulfonyl-3-(4-fluorobenzoyl)-4,4-dimethyl-dihydropyrrole in which R is 4-fluoro:

[0047] (1) In a 10mL dry reaction tube, add the raw material N-2-methylallyl-N-3-(4-fluorophenyl)-propargyl p-toluenesulfonamide (0.179g , 0.5mmol), Fe(acac) 3 (0.1mmol), tert-butyl nitrite (0.103g, 1mmol), polymethylsiloxane (0.333g, 1.5mmol) and 10mL tetrahydrofuran, and the mixed system was reacted at 60°C for 24 hours. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure to obtain a crude product.

[0048] (2) Next, the crude product was dissolved in 10 mL of acetonitrile-water (9:1 by volume) solution, and a catalytic amount of iodine (12 mg) and hydrogen peroxide (1 mmol) were added, and reac...

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Abstract

The invention discloses a preparation method of a polysubstituted pyrroline compound, and belongs to the technical field of fine chemical engineering. According to the method, N-2-methylallyl-N-3-arylpropargyl p-toluenesulfonamide is used as a raw material, a specific ferric salt is used as a catalyst, tert-butyl nitrite is used as an oxidizing agent, polymethylsiloxane (PMHS) is used as a hydrogen source, and a reaction is carried out in an inert atmosphere; and then a reaction is performed in an I2 / H2O2 system to synthesize a target product, namely the polysubstituted pyrroline compound. The method has the advantages of cheap catalyst, mild reaction condition and the like, and has a good application prospect.

Description

technical field [0001] The invention relates to a preparation method of multi-substituted dihydropyrrole compounds, belonging to the technical field of fine chemicals. Background technique [0002] As a very important class of five-membered nitrogen-containing heterocyclic compounds, dihydropyrrole widely exists in the molecular skeletons of natural products and bioactive drugs; , energy conservation and conversion, information transmission and the body's autoimmunity and other processes) play a vital role. At the same time, pyrrole compounds are also widely used in research fields such as medicine, pesticides, materials, and daily chemicals. Therefore, the synthesis of pyrrole derivatives has attracted more and more attention from organic synthetic chemists. [0003] Although there have been many reports on the synthesis of dihydropyrrole derivatives in the literature, the synthesis of most substituted dihydropyrrole derivatives still needs to be carried out under noble me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/48
CPCC07D207/48
Inventor 夏晓峰王大伟
Owner JIANGNAN UNIV
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