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Synthesis method of [60]fullerene dihydropyrrole derivative

A technology of fullerene dihydropyrroline and synthesis method is applied in the field of synthesis of [60]fullerene dihydropyrrole derivatives, and can solve the diversity limitation of fullerene dihydropyrroline derivatives, alkynedioic acid dihydrogen The problem of single methyl ester and other problems can achieve the effect of wide substrate applicability and good functional group compatibility.

Inactive Publication Date: 2017-09-01
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in this reaction, because wherein component dimethyl alkyndioate is single, fixed
Therefore, in a real sense, this multi-component reaction is also limited in the diversity of synthesizing fullerene dihydropyrroline derivatives.

Method used

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  • Synthesis method of [60]fullerene dihydropyrrole derivative
  • Synthesis method of [60]fullerene dihydropyrrole derivative
  • Synthesis method of [60]fullerene dihydropyrrole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of fullerene dihydropyrrolidine derivative A:

[0018]

[0019] Reaction steps:

[0020] Will C 60 (0.05mmol), (0.10mmol), Ag 2 CO 3 (0.015mmol) and Cs 2 CO 3 (0.10mmol) was added to a dry 25mL dry reaction test tube, then added o-dichlorobenzene (7mL) and acetonitrile (1mL), ultrasonically dissolved, screwed on the cock, and then placed in an oil bath at 115°C for heating and stirring. , TLC detection reaction. After two hours the reaction was complete. The system was wet-loaded through a short silica gel column, toluene was used as the eluent to remove insoluble substances in the system, and the system was distilled and spin-dried under reduced pressure. Wash the remaining solid with CS 2 Dissolving, loading, and passing through the column, first use CS 2 Unreacted C was collected as eluent 60 , then to CS 2 / CH 2 Cl 2 Elution as eluent gave product A in a relative yield of 36%.

[0021] A: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ7.57(d, J=8....

Embodiment 2

[0026] Preparation of fullerene dihydropyrrolidine derivative B:

[0027]

[0028] Reaction steps:

[0029] Will C 60 (0.05mmol), (0.10mmol), Ag 2 CO 3 (0.015mmol) and Cs 2 CO 3 (0.10mmol) was added to a dry 25mL dry reaction test tube, then added o-dichlorobenzene (7mL) and acetonitrile (1mL), ultrasonically dissolved, screwed on the cock, and then placed in an oil bath at 115°C for heating and stirring. , TLC detection reaction. After two hours the reaction was complete. The system was wet-loaded through a short silica gel column, toluene was used as the eluent to remove insoluble substances in the system, and vacuum distillation and spin-drying were performed. Wash the remaining solid with CS 2 Dissolving, loading, and passing through the column, first use CS 2 Unreacted C was collected as eluent 60 , then to CS 2 / CH2 Cl 2 Elution as eluent gave product B in a relative yield of 35%.

[0030] B: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ6.92(d, J=1.6Hz, 1H), 6.80...

Embodiment 3

[0035] Preparation of fullerene dihydropyrrolidine derivative C:

[0036]

[0037] Reaction steps:

[0038] Will C 60 (0.05mmol), (0.10mmol), Ag 2 CO 3 (0.015mmol) and Cs 2 CO 3 (0.10mmol) into a dry 25mL dry reaction test tube, then add o-dichlorobenzene (7mL) and (1 mL), sonicate to dissolve it, screw on the cock, and then place it in an oil bath at 115° C. to heat and stir to react, and TLC detects the reaction. After two hours the reaction was complete. The system was wet-loaded through a short silica gel column, toluene was used as the eluent to remove insoluble substances in the system, and the system was distilled and spin-dried under reduced pressure. Wash the remaining solid with CS 2 Dissolving, loading, and passing through the column, first use CS 2 Unreacted C was collected as eluent 60 , then to CS 2 / CH 2 Cl 2 Elution as eluent gave product C in a relative yield of 32%.

[0039] C: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ8.39(d, J=8.8Hz, 2H), 8.13(...

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Abstract

The invention discloses a synthesis method of a [60]fullerene dihydropyrrole derivative, and belongs to the technical field of synthesis of fullerene derivatives. The synthesis method of the [60]fullerene dihydropyrrole derivative, disclosed by the invention, is characterized in that a specific process comprises the following steps: by taking [60]fullerene, a sulfonyl hydrazone compound and a nitrile compound as reaction raw materials, carrying out cyclization reaction at 110 DEG C to 120 DEG C under the acceleration effect of Ag (I) to prepare a target product, i.e., the [60]fullerene dihydropyrrole derivative. The synthesis process disclosed by invention has wide substrate applicability and relatively good functional group compatibility, and can be used for synthesizing fullerene macromolecular compounds; the reaction can be used for synthesizing raw materials, which are simple and easy to obtain, into the fullerene derivative with various substituent groups.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fullerene derivatives, in particular to a synthesis method of [60] fullerene dihydropyrrole derivatives. Background technique [0002] Molecular frameworks with diverse substituents are often required in the fields of materials and medicine, and multicomponent reactions catalyzed and promoted by transition metals have been developed as powerful tools for the construction of such molecules. However, in the reported transition metal-catalyzed and promoted fullerene functionalization reactions, including free radical reactions, asymmetric reactions, coupling reactions, and carbon-hydrogen bond activation reactions, almost all reactions are single-component to fullerene Addition reactions, which limit the diversity of functional groups that can be incorporated to a certain extent. In this way, it will be an ideal and challenging direction to develop a multi-component reaction strategy with trans...

Claims

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Application Information

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IPC IPC(8): C07D209/96C07D403/10
CPCC07D209/96C07D403/10
Inventor 张朋玲刘统信时蕾麻娜娜刘青锋张志国
Owner HENAN NORMAL UNIV
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