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Synthesis method of triarylmethane derivative

A technology of triarylmethane and synthesis method, which is applied in the field of synthesis of triarylmethane derivatives, can solve the problems of limited reaction substrate range, poor regioselectivity, severe reaction conditions, etc., and achieves good stereoselectivity and reaction time. Effects with short, simple composition steps

Active Publication Date: 2020-08-04
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are some obvious deficiencies in the above synthetic methods, such as: limited reaction substrate range, poor regioselectivity, expensive transition metals are often used in the reaction, multi-step reaction and harsh reaction conditions are required, etc.

Method used

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  • Synthesis method of triarylmethane derivative
  • Synthesis method of triarylmethane derivative
  • Synthesis method of triarylmethane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of synthetic method of triarylmethane derivative ((4-dimethylaminophenyl) (2-hydroxyphenyl) (phenyl) methane), comprises the following steps:

[0037]

[0038] 1.0mmol (0.122g) salicylaldehyde, 1.0mmol (0.122g) phenylboronic acid, 1.2mmol (0.102g) piperidine, 1.2mmol (0.145g) N, N-dimethylaniline and 0.5mmol (0.127g) ) catalyst (catalyst is I 2 ) into a 10ml dry round-bottomed flask, then add 1ml chlorobenzene as a solvent, heat to reflux at 100°C, monitor the reaction by TLC, after the reaction is complete, cool to room temperature, add 30ml ethyl acetate to the reaction system, and use 20ml Washed with water and 10ml saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered, and after a large amount of solvent was evaporated under reduced pressure, the residue was separated by column chromatography, using n-hexane and ethyl acetate as eluents, and the solvent Evaporated and dried to obtain the target compound, the reaction yield w...

Embodiment 2

[0040] A kind of synthetic method of triarylmethane derivative ((4-dimethylaminophenyl) (2-hydroxyl-4 fluorophenyl) (phenyl) methane), comprises the following steps:

[0041]

[0042] 1.0mmol (0.140g) 5-fluoro salicylaldehyde, 1.0mmol (0.122g) phenylboronic acid, 1.2mmol (0.102g) piperidine, 1.2mmol (0.145g) N,N-dimethylaniline and 0.5mmol (0.127g) catalyst (catalyst is I 2 ) into a 10ml dry round-bottomed flask, then add 1ml chlorobenzene as a solvent, heat to reflux at 100°C, monitor the reaction by TLC, after the reaction is complete, cool to room temperature, add 30ml ethyl acetate to the reaction system, and use 20ml Washed with water and 10ml saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered, and after a large amount of solvent was evaporated under reduced pressure, the residue was separated by column chromatography, using n-hexane and ethyl acetate as eluents, and the solvent Evaporated and dried to obtain the target compound, the ...

Embodiment 3

[0044] A kind of synthetic method of triarylmethane derivative ((4-dimethylaminophenyl) (2-hydroxyl-4 chlorophenyl) (phenyl) methane), comprises the following steps:

[0045]

[0046] 1.0mmol (0.156g) 5-chloro salicylaldehyde, 1.0mmol (0.122g) phenylboronic acid, 1.2mmol (0.102g) piperidine, 1.2mmol (0.145g) N, N-dimethylaniline and 0.5mmol (0.127g) catalyst (catalyst is I 2 ) into a 10ml dry round-bottomed flask, then add 1ml chlorobenzene as a solvent, heat to reflux at 100°C, monitor the reaction by TLC, after the reaction is complete, cool to room temperature, add 30ml ethyl acetate to the reaction system, and use 20ml Washed with water and 10ml saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered, and after a large amount of solvent was evaporated under reduced pressure, the residue was separated by column chromatography, using n-hexane and ethyl acetate as eluents, and the solvent Evaporated and dried to obtain the target compound, the...

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Abstract

The invention discloses a method for synthesizing a triarylmethane derivative. The triarylmethane derivative is synthesized through a one-pot reaction of various substituted salicylaldehyde, aromaticboric acid and aromatic hydrocarbon by using iodine as a catalyst. The three different aryl groups are introduced from salicylaldehyde, arylboronic acid and aromatic hydrocarbon which are low in priceand easy to obtain in one step under the condition of no alkali / ligand and completely without participation of metal catalysis, the reaction has very high chemical selectivity, and a triarylmethane derivative with completely asymmetric groups is provided. The method has the advantages of simple operation, short reaction time, cheap and easily available catalyst, low production cost, less pollution, simple post-treatment, and very high yield of the reaction.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of triarylmethane derivatives. Background technique [0002] Triarylmethane derivatives are widely used in medicinal chemistry, dye industry and material science due to their special structure. They are a very important class of compounds. So far, the commonly used method for synthesizing triarylmethane derivatives is mainly: through the Friedel-Crafts alkylation method, diarylmethanol (ester, ether, imine, etc.) is directly reacted with aromatic hydrocarbons. Containing electron-donating groups is easy to react, the reaction substrate has certain limitations, and is prone to isomer by-products; another synthesis method is through cross-coupling reactions or transition metal-catalyzed carbon-hydrogen functionalization reactions Synthetic; Another method is through the 1,6-addition arylation of benzoquinone derivatives to synthesis. There...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C215/74C07C217/80C07D333/20C07D295/096C07B37/04
CPCC07C213/08C07D333/20C07D295/096C07B37/04C07C215/74C07C217/80
Inventor 于雅琴徐大振
Owner TIANJIN NORMAL UNIVERSITY
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