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A kind of visible light catalytic method for synthesizing pyrrol-4-one derivatives

A technology of visible light and derivatives, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problems of high equipment requirements, high cost, unfriendly environment, etc. Concise, low-dosage effect

Active Publication Date: 2019-09-27
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These restrictive factors have led to the above-mentioned method having high requirements on the device, high cost and unfriendly to the environment, and cannot be applied on a large scale or industrialized.

Method used

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  • A kind of visible light catalytic method for synthesizing pyrrol-4-one derivatives
  • A kind of visible light catalytic method for synthesizing pyrrol-4-one derivatives
  • A kind of visible light catalytic method for synthesizing pyrrol-4-one derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A method for visible light catalytic synthesis of pyrrol-4-one, comprising the steps of:

[0056] 0.2 mmol cis ethyl 3-phenyl-3-(anilino)acrylate, 3.0 mg of photocatalyst 1 and 14.7 mg of zinc trifluoromethanesulfonate (Zn(OTf) 2 ) was added to 3mL of 1,4-dioxane to obtain solution A, and the concentration of photocatalyst 1 in the solution A was 1.3×10 -3 mol / L, the concentration of zinc trifluoromethanesulfonate is 1.3×10 -2 mol / L; In the air environment at room temperature, the solution A was irradiated with visible light for 1 h to react, and after the reaction was completed, rotary evaporation and column chromatography were carried out to obtain pyrrol-4-one.

[0057] Described pyrrole-4-ketone is through the nuclear magnetic hydrogen spectrogram ( figure 1 )﹑carbon spectrum ( figure 2 ) and mass spectrum ( image 3 ) was determined to be ethyl 3-oxa-2,5-diphenyl-1-phenyl-2,3-dihydro-1H-pyrrole-2,4-dicarboxylate, and the conversion rate of the raw material was...

Embodiment 2 to 34

[0063] Except for the contents shown in Table 1, other pyrrol-4-ones were synthesized in the same manner as in Example 1.

[0064] The results of determination of the pyrrol-4-one by proton nuclear magnetic spectrum, carbon spectrogram and mass spectrogram are shown in Table 1.

[0065] Each parameter of table 1 synthetic pyrrol-4-ketone, concrete name and productive rate of pyrrol-4-ketone

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

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Abstract

The invention discloses a method for catalytic synthesis of pyrrole-4-ketone with visible light. The method comprises the following steps: adding enamine, a photocatalyst and a metal catalyst into an organic solvent so as to obtain a solution A; allowing visible right to irradiate the solution A under the condition of air, and carrying out a reaction; and after completion of the reaction, carrying out separation so as to obtain the pyrrole-4-ketone. The method provided by the invention combines visible-light catalysis with metal catalysis, can be realized through visible-light irradiation in an air environment, is simple and highly-efficient in the whole process and has mild reaction conditions; the photocatalyst is cheap and has small usage amount; and application values are achieved in an organic reaction and industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing pyrrolidone. More specifically, it relates to a method for the visible light catalytic synthesis of a series of pyrrol-4-ones. Background technique [0002] Pyrrol-4-ones are an important class of structural skeletons that widely exist in biologically active substances and natural products. In the 1990s, Smith and Hirschmann discovered the peptide mimics constructed by pyrrol-4-one, which showed good inhibitory effect on HIV-1 virus. Pyrrol-4-ones are an important class of organic synthons. Based on the importance of this type of backbone molecule, several related synthetic methods have been reported, including: [2+3] reaction of cyclopropanone with imine; oxidative cyclization reaction of enamine under strong oxidant and high temperature; 3-hydroxy Alkylation reaction in pyrrole molecule; condensation reaction of amino acid ester and aldehyde, etc. Nevertheless, these methods often require harsh c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34B01J31/04B01J31/22
CPCC07D207/34B01J31/04B01J31/22B01J31/0228B01J2531/0238B01J2531/827B01J2531/821B01J2540/22B01J35/39
Inventor 佟振合雷涛吴骊珠周超
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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