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Epoxy-containing skeleton nitrile compound and synthesis method thereof

A synthesis method and technology for nitrile compounds, applied in the direction of organic chemistry, etc., can solve the problems such as furan compounds that have not yet been found

Inactive Publication Date: 2018-07-06
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] As mentioned above, multiple furan compounds and synthetic methods thereof are disclosed in the prior art, but up to now, there is no report of using nitrile compounds containing epoxy skeleton to prepare furan compounds. Therefore, the present invention provides a novel The epoxy-skeleton-containing nitrile compound found that it can be used to synthesize furan compounds, thus expanding the synthetic route of furan compounds, which has good research value

Method used

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  • Epoxy-containing skeleton nitrile compound and synthesis method thereof
  • Epoxy-containing skeleton nitrile compound and synthesis method thereof
  • Epoxy-containing skeleton nitrile compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] The reaction route is:

[0077]

[0078] Specific steps are as follows:

[0079] S1: At room temperature, add 100mmol of the compound of the above formula (1), 150mmol of the compound of the above formula (2), 10mmol of palladium acetate, 5mmol of 2,2'-bipyridine, 250mmol of silver acetate and 600mmol of trifluoro to an appropriate amount of organic solvent tetrahydrofuran (THF) Acetic acid, then stirred and warmed up to 70 ° C, and stirred and reacted at this temperature for 40 hours;

[0080] After the reaction was finished, the reaction mixture was poured into a sufficient amount of ethyl acetate, then washed with saturated brine, and the organic layer and the water layer were separated. After the water layer was fully extracted with ethyl acetate, the organic layers were combined (after washing with saturated brine). The organic layer and the organic layer obtained by ethyl acetate extraction), with anhydrous Na 2 SO 4 Drying, distillation under reduced pressu...

Embodiment 2

[0086] The reaction route is:

[0087]

[0088] Specific steps are as follows:

[0089]S1: At room temperature, add 100mmol of the compound of the above formula (1), 250mmol of the compound of the above formula (2), 3mmol of palladium acetate, 15mmol of 2,2'-bipyridine, 150mmol of silver acetate and 1000mmol of trifluoro to an appropriate amount of organic solvent tetrahydrofuran (THF) Acetic acid, then stirred and warmed up to 100 ° C, and stirred and reacted at this temperature for 20 hours;

[0090] After the reaction was finished, the reaction mixture was poured into a sufficient amount of ethyl acetate, then washed with saturated brine, and the organic layer and the water layer were separated. After the water layer was fully extracted with ethyl acetate, the organic layers were combined (after washing with saturated brine). The organic layer and the organic layer obtained by ethyl acetate extraction), with anhydrous Na 2 SO 4 Drying, distillation under reduced press...

Embodiment 3

[0096] The reaction route is:

[0097]

[0098] Specific steps are as follows:

[0099] S1: At room temperature, add 100mmol of the compound of the above formula (1), 200mmol of the compound of the above formula (2), 6.5mmol of palladium acetate, 10mmol of 2,2'-bipyridyl, 200mmol of silver acetate and 800mmol of three Fluoroacetic acid, then stirred and heated to 85 ° C, and stirred and reacted at this temperature for 30 hours;

[0100] After the reaction was finished, the reaction mixture was poured into a sufficient amount of ethyl acetate, then washed with saturated brine, and the organic layer and the water layer were separated. After the water layer was fully extracted with ethyl acetate, the organic layers were combined (after washing with saturated brine). The organic layer and the organic layer obtained by ethyl acetate extraction), with anhydrous Na 2 SO 4 Drying, distillation under reduced pressure, the residue is eluted by flash column chromatography (with a m...

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Abstract

The invention relates to an epoxy-containing skeleton nitrile compound as shown in the following formula (4) and a synthesis method thereof. The synthesis method adopts the following reaction route: FORMULA, and comprises the following steps: S1: reacting a compound of a formula (1) with a compound of formula (2) in an organic solvent in the presence of a palladium catalyst, an organic ligand, anoxidizing agent and an acidic compound, performing post-treatment after finishing reaction to obtain a compound of formula (3); and S2: performing self-cyclization reaction on the compound of formula(3) in the organic solvent in the presence of the oxidizing agent, performing post-treatment after finishing reaction to obtain a compound of formula (4). The method creatively optimizes multiple technical features in each step so as to provide a novel synthesis method and synthesis route for preparation of such compounds and have excellent industrial prospects and potential application values.

Description

technical field [0001] The invention relates to a synthesis method of a condensed heterocyclic compound, in particular to a nitrile compound containing an epoxy skeleton and a synthesis method thereof, belonging to the field of organic chemical synthesis. Background technique [0002] Epoxy compounds have important applications in the technical field of organic synthesis. They can be used to prepare various follow-up products through various reactions such as ring opening, and have important applications in the technical field of organic synthesis. [0003] In addition, in the field of organic chemistry, the furan ring is an important structural unit and the building unit of pharmaceutical compounds, and furan rings are included in various active drugs. A lot of in-depth research on furan compounds has been carried out, and many achievements have been made, such as: [0004] CN101148442A discloses a histone acetylase inhibitor of the following formula comprising a furan uni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/38C07D307/38C07D307/42C07D307/36
CPCC07D303/38C07D307/36C07D307/38C07D307/42
Inventor 宫巨林陈久喜张业彤邵银林胡堃叶鹏清许彤于书玲胡茂林程天行
Owner WENZHOU UNIVERSITY