Method for synthesizing trifluoromethyl-1,2,4-triazinone compound through copper catalyzed synthesis

A technology of trifluoromethyl and triazinone, which is applied in the field of organic fluorine chemical synthesis and achieves the effects of good adaptability, high yield and mild reaction conditions

Inactive Publication Date: 2017-09-01
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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At present, there are no reports on the efficient and simple synthe...

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  • Method for synthesizing trifluoromethyl-1,2,4-triazinone compound through copper catalyzed synthesis
  • Method for synthesizing trifluoromethyl-1,2,4-triazinone compound through copper catalyzed synthesis
  • Method for synthesizing trifluoromethyl-1,2,4-triazinone compound through copper catalyzed synthesis

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Experimental program
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Embodiment 1

[0021] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a 5 mL reaction tube, add 0.025 mmol cuprous iodide, 1 mL tetrahydrofuran, 0.5 mmol phenylacetylene, 0.65 mmol 1-azido-3-benzene Propane, 0.75 mmol trifluoroacetic anhydride, finally add 1 mmol triethylamine, stir and react in a closed system at room temperature for 9 h, filter with 100-200 mesh silica gel, rinse with dichloromethane, combine the organic phases, and spin The organic solvent was removed by evaporation; the obtained crude product was eluted with n-pentane and ethyl acetate by silica gel column chromatography to obtain 6-phenyl-(3'-phenylpropyl)-3-(trifluoromethyl) -1,2,4-triazine-5(4 H )-ketone (90% isolated yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.28 (d, J = 7.8 Hz, 2H), 7.54 (t,1H), 7.47 (t, J = 7.5 Hz, 2H), 7.29 (t, J = 7.4 Hz, 2H), 7.20 (t, J = 6.8 Hz,3H), 4.08 (t, 2H), 2.76 (t, J = 7.6 Hz, 2H), 2.20 – 2.01 (dt, 2H). 19 F NMR (376 MHz, CDCl 3 ) δ -65.5 (s, 3F).

Embodiment 2

[0023] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a 5 mL reaction tube, add 0.025 mmol cuprous iodide, 1 mL tetrahydrofuran, 0.5 mmol 4-tert-butylphenylacetylene, 0.65 mmol 1-azide Base-3-phenylpropane, 0.75mmol trifluoroacetic anhydride, finally add 1 mmol triethylamine, stir and react in a closed system at room temperature for 9 h, filter with 100-200 mesh silica gel, wash with dichloromethane, and combine Organic phase, and then the organic solvent was removed by rotary evaporation; the obtained crude product was eluted with n-pentane and ethyl acetate to obtain 6-(4'-(tert-butyl)phenyl)-4-( 3''-phenylpropyl)-3-(trifluoromethyl)-1,2,4-triazine-5(4 H )-ketone (86% isolated yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.30 (d, J = 8.6 Hz, 2H), 7.56 (d, J = 8.6 Hz, 2H), 7.34 (t, 2H), 7.25 (t, J = 6.2 Hz,3H), 4.13 (t, 2H), 2.81 (t, J = 7.6 Hz, 2H), 2.26 – 2.03 (dt, 2H), 1.41 (s,9H). 19 F NMR (376 MHz, CDCl 3 ) δ -65.5 (s, 3F).

Embodiment 3

[0025] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a 5 mL reaction tube, add 0.025 mmol cuprous iodide, 1 mL tetrahydrofuran, 0.5 mmol 4-ethynyl phenpentyl ether, 0.65 mmol 1-azide Base-3-phenylpropane, 0.75mmol trifluoroacetic anhydride, finally add 1 mmol triethylamine, stir and react in a closed system at room temperature for 9 h, filter with 100-200 mesh silica gel, wash with dichloromethane, and combine Organic phase, and then the organic solvent was removed by rotary evaporation; the obtained crude product was eluted with n-pentane and ethyl acetate by silica gel column chromatography to obtain 6-(4'-(pentyloxy)phenyl)-4-( 3''-phenylpropyl)-3-(trifluoromethyl)-1,2,4-triazine-5(4 H )-ketone (83% isolated yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.41 (d, J = 9.0 Hz, 2H), 7.32 (t, 2H), 7.24 (t, J = 5.8 Hz, 3H), 6.99 (d, J = 9.0 Hz,2H), 4.16 – 3.91 (m, 4H), 2.78 (t, J = 7.6 Hz, 2H), 2.12 (dt, J = 15.6, 7.8Hz, 2H), 1.93 – 1.73 (m, 2H), 1.57 – 1.3...

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Abstract

The invention discloses a method for synthesizing a trifluoromethyl-1,2,4-triazinone compound through copper catalyzed synthesis. The method comprises the following steps: by taking copper salt as a catalyst, and nitrine, alkyne and trifluoroacetic anhydride as raw materials, adding triethylanmine, stirring for 1-16 hours at room temperature in a tetrahydrofuran solvent, and after the reaction is completed, treating a reaction liquid, thereby obtaining the trifluoromethyl-1,2,4-triazinone compound. The synthesis method disclosed by the invention has the advantages of being cheap in catalyst price, low in toxicity, gentle in reaction condition, high in yield, easy in raw material obtaining, simple and convenient to operate, high in functional group universality and the like, and has good industrial application prospects.

Description

technical field [0001] The invention belongs to the field of organic fluorine chemical synthesis, and in particular relates to a copper-catalyzed method for synthesizing trifluoromethyl-1,2,4-triazone compounds. Background technique [0002] The introduction of trifluoromethyl groups into organic molecules can enhance the lipid solubility of molecules, improve metabolic stability, oxidation resistance and rigidity, etc. Therefore, compounds containing trifluoromethyl groups are widely used in the fields of medicine, pesticides, and advanced materials. On the other hand, 1,2,4-triazinone compounds have good biological activities in insecticide, bactericide, anticancer, antiulcer and plant growth regulation. The construction of trifluoromethyl-containing 1,2,4-triazone compounds has important theoretical research significance and practical application value. At present, there is no report on the efficient and simple synthesis of such compounds through some cheap and easy-to-o...

Claims

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Application Information

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IPC IPC(8): C07D253/07C07D409/06
Inventor 翁志强吴伟王君雯
Owner FUZHOU UNIV
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