Trifluoroacetyl substituted hydrazone derivative and synthesis method thereof

A technique for the synthesis of trifluoroacetyl groups, which is applied in the field of trifluoroacetyl substituted hydrazone derivatives and their synthesis, can solve problems such as blanks, and achieve the effects of simple operation, mild reaction conditions, and high product yields

Active Publication Date: 2019-01-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, simple N-aryl-trifluoroacetyl substituted hydrazone compounds and their synthesis methods have not been reported, and the research on such compounds and their synthesis techn

Method used

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  • Trifluoroacetyl substituted hydrazone derivative and synthesis method thereof
  • Trifluoroacetyl substituted hydrazone derivative and synthesis method thereof
  • Trifluoroacetyl substituted hydrazone derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 25ml reaction flask, add 0.2mmol of p-methoxyphenyldiazonium tetrafluoroborate, 0.3mmol of triethylenediamine, 0.3mmol of 3-phenyl-1,1,1,-trifluoro Acetone, 2 ml of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether: ethyl acetate with a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 97%.

Embodiment 2

[0031] In a 25ml reaction flask, add 0.2mmol of p-methoxyphenyldiazonium tetrafluoroborate, 0.3mmol of triethylenediamine, 0.3mmol of 3-phenyl-1,1,1,-trifluoro Acetone, 2 ml of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with methylene chloride, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether:ethyl acetate in a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 97%.

Embodiment 3

[0033] In a 25 ml reaction flask, add 0.2 mmol p-methoxyphenyldiazonium hexafluorophosphate, 0.3 mmol potassium carbonate, 0.3 mmol 3-phenyl-1,1,1,-trifluoroacetone, 2 mL of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether: ethyl acetate with a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 64%.

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a trifluoroacetyl substituted hydrazone derivative and a synthesis method thereof. The trifluoroacetyl substituted hydrazone derivative has a structural formula shown as a formula (I); the synthesis method of the trifluoroacetyl substituted hydrazone derivative comprises the following steps: adding diazotate, trifluoromethyl ketone, alkali and a solvent into a reactor; stirring and reacting at 0 to 70 DEG C for 0.05 to 24h; after reaction is finished, cooling to room temperature; adding water and an organic solventand extracting a reaction solution; evaporating to remove the solvent, so as to obtain a crude product; and carrying out column chromatography purification to obtain the trifluoroacetyl substituted hydrazone derivative. The synthesis method provided by the invention does not utilizes a catalyst and does not need a ligand, and all raw materials have no toxicity and are cheap and easy to obtain; the reaction has good adaptability on functional groups, wide substrate adaptability and high product yield; and the synthesis method is simple and safe to operate and has moderate reaction conditions and a good industrial application prospect. The formula (I) is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a trifluoroacetyl-substituted hydrazone derivative and a synthesis method thereof. Background technique [0002] In view of the small atomic radius and high electronegativity of fluorine atoms, it is difficult to be polarized. Therefore, the introduction of fluorine atoms or fluorine-containing groups into organic compound molecules usually significantly improves the chemical properties, physical properties and biological activities of the compounds. According to statistics, more than 30% of the pesticide or drug molecules sold on the market contain at least one fluorine atom or fluorine-containing group. However, the types of fluorine-containing natural products existing in nature are very limited. In order to meet the urgent needs of people's production and research on the increase in the number and types of organic fluorinated compounds, the development ...

Claims

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Application Information

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IPC IPC(8): C07C251/86C07C249/16C07C317/34C07C315/04C07D215/38
CPCC07C249/16C07C251/86C07C315/04C07C317/34C07D215/38
Inventor 竺传乐江焕峰
Owner SOUTH CHINA UNIV OF TECH
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