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A cyano-substituted biaryl ring derivative and its preparation method

A technology of cyano substitution and biaryl ring, which is applied in the field of organic synthesis, can solve the problems of poor compatibility and many by-products, and achieve the effect of increasing complexity, simple substrate and simple operation

Active Publication Date: 2021-11-26
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In view of this, the present invention provides a cyano-substituted biaryl ring derivative and a preparation method thereof, which can effectively solve the technical problems of poor compatibility and many by-products in the preparation of existing cyano-containing biaryl rings

Method used

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  • A cyano-substituted biaryl ring derivative and its preparation method
  • A cyano-substituted biaryl ring derivative and its preparation method
  • A cyano-substituted biaryl ring derivative and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0053] In this example, the preparation of 2-[5-([2,2′-bithiophene)]-benzonitrile (1a) is carried out, and its reaction formula is as follows:

[0054]

[0055] Under the air atmosphere, the aromatic imide ester compound 2a (0.2mmol, 30mg) shown in the formula II, the thiophene compound 3a (0.5mmol, 84mg) shown in the formula III, and pentamethylcyclopentadiene were sequentially added into the reactor. Rhodium chloride dimer (0.004mmol, 2.5mg), bistrifluoromethanesulfonimide silver salt (0.01mmol, 4.0mg), sodium acetate (0.03mmol, 2.5mg), pivalic acid (0.06mmol, 6.2mg) of N,N'-dimethylformamide (1.0mL) solution was added to the reactor, the reactor was placed on the reaction device and the temperature was adjusted to 130°C, and the reaction was carried out for 18h, and determined by thin layer chromatography analysis After the reaction is finished, the reaction solution is suction-filtered with diatomaceous earth and concentrated into a dry powder with 400-mesh silica gel t...

Embodiment 2

[0061] In this example, the preparation of 2-[5-([2,2′-bithiophene)]-4-fluorobenzonitrile (1b) is carried out, and its reaction formula is as follows:

[0062]

[0063] Under the air atmosphere, add aromatic imine ester compound 2b (0.2mmol) shown in formula II, thiophene compound 3a (0.5mmol) shown in formula III, pentamethylcyclopentadienyl rhodium chloride successively in the reactor Dimer (0.004mmol, 2.5mg), bistrifluoromethanesulfonimide silver salt (0.01mmol, 4.0mg), sodium acetate (0.03mmol, 2.5mg), pivalic acid (0.06mmol, 6.2mg) N,N'-dimethylformamide (1.0mL) solution was added to the reactor, the reactor was placed on the reaction device and the temperature was adjusted to 140°C, and the reaction was carried out for 12 hours. It was determined by thin layer chromatography that the reaction was complete. The reaction solution was suction-filtered with diatomaceous earth, concentrated with 400-mesh silica gel by rotary evaporation to make a dry powder, and then the r...

Embodiment 3

[0069] In this example, the preparation of 2-[5-([2,2′-bithiophene)]-4-chlorobenzonitrile (1c) is carried out, and its reaction formula is as follows:

[0070]

[0071] Under the air atmosphere, in the reactor, sequentially add aromatic imine ester compound 2c (0.2mmol) shown in formula II, thiophene compound 3a (0.5mmol) shown in formula III, pentamethylcyclopentadienyl rhodium chloride Dimer (0.004mmol, 2.5mg), bistrifluoromethanesulfonimide silver salt (0.01mmol, 4.0mg), sodium acetate (0.03mmol, 2.5mg), pivalic acid (0.06mmol, 6.2mg) N,N'-dimethylformamide (1.0mL) solution was added to the reactor, the reactor was placed on the reaction device and the temperature was adjusted to 140°C, and the reaction was carried out for 12 hours. It was determined by thin layer chromatography that the reaction was complete. The reaction solution was suction-filtered with diatomaceous earth, concentrated with 400-mesh silica gel by rotary evaporation to make a dry powder, and then the ...

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Abstract

The invention belongs to the technical field of organic synthesis, in particular to a cyano-substituted biaryl ring derivative and a preparation method thereof. The present invention provides a cyano-substituted biaryl ring derivative whose structural formula is shown in formula I. The present invention also provides a method for preparing a cyano-substituted biaryl ring derivative, comprising: dissolving the compound represented by the formula II and the compound represented by the formula III in an inert solvent, under the action of an oxidant and a metal catalyst, adding base and react under alkaline conditions to obtain a cyano-substituted biaryl ring derivative; the invention provides a cyano-substituted biaryl ring derivative and a preparation method thereof, which can effectively solve the problem of the existing cyano group-containing biaryl ring derivatives. There are technical problems such as the lack of the preparation method of the biaryl ring, the poor compatibility of the existing scheme, the cumbersome steps and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a cyano-substituted biaryl ring derivative and a preparation method thereof. Background technique [0002] Biaryl rings are a class of dominant skeletons that widely exist in molecules of important drugs and functional materials. In the "Comprehensive Medicinal Chemistry Database" published in 1996, biaryl rings were listed to exhibit different medicinal effects, such as ascorbic acid, antifungal, Anti-tumor, anti-high cholesterol, anti-hyperlipidemia, anti-anemia, anti-fasciitis, anti-rheumatism, analgesic, anti-inflammatory, anti-thrombotic, anti-uric acid and other effects. Not only that, in the existing drugs, the biaryl ring structure skeleton accounts for 4.3%. On the other hand, thiophene compounds such as bithiophene, terthiophene, and dithiophene[3,2-B:2′,3′-D]thiophene are key skeletons of a class of optoelectronic materials, electronic chemicals and organic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/24C07D495/14
CPCC07D333/24C07D495/14
Inventor 欧阳文森李先纬霍延平
Owner GUANGDONG UNIV OF TECH