A kind of preparation method of 2-(2,2,2-trifluoroethyl)-3-aryl-2h-azapropenidine compound

A trifluoroethyl compound technology, applied in the field of compound preparation, can solve the problems of limited application, expensive, unstable, etc.

Active Publication Date: 2020-04-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently synthesized containing CF 3 There are fewer reports on substituted 2H-aziridine compounds (Angew.Chem.Int.Ed. 2015, 54, 9356.; Adv.Synth.Catal.2015, 357, 3069.)
At the same time, these methods use the expensive and unstable CF 3 Methylation reagents, which greatly limit the application of such methods

Method used

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  • A kind of preparation method of 2-(2,2,2-trifluoroethyl)-3-aryl-2h-azapropenidine compound
  • A kind of preparation method of 2-(2,2,2-trifluoroethyl)-3-aryl-2h-azapropenidine compound
  • A kind of preparation method of 2-(2,2,2-trifluoroethyl)-3-aryl-2h-azapropenidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 1-Phenyl-1-azido-4,4,4-trifluoro-1-butene (compound 1)

[0061] At room temperature, 167 mg (0.5 mmol) of 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene, dichloromethane, and (2.5 mL), potassium fluoride (34.9 mg, 0.6 mmol), 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene 1.2 times the molar amount, Phenyl-2-trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene 5-fold molar amount of trimethylsilyl azide (0.33 mL, 2.5 mmol). Under the condition of stirring, slowly add 1,8-diazabicyclodeca Monocarb-7-ene (diluted in 2.5 mL dichloromethane). After stirring and reacting at 25°C for 1 h, it was extracted with ethyl acetate (3×10mL), the combined organic phases were washed with saturated brine (2×10mL) and dried with anhydrous magnesium sulfate, and the target compound was obtained by column chromatography. The filler was Silica gel, the eluent is petroleum ether, and the separation yield is 63%.

Embodiment 2

[0063] 1-(4-methylphenyl)-1-azido-4,4,4-trifluoro-1-butene (compound 2)

[0064] Except that the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 is replaced by the same molar amount of 4-(4-methylphenyl) Except for -2-trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene, the same method as in Example 1 was followed to obtain the target compound in an isolated yield of 68%.

Embodiment 3

[0066] 1-(4-isopropylphenyl)-1-azido-4,4,4-trifluoro-1-butene (compound 3)

[0067] In addition to changing the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 to the same molar amount of 4-(4-isopropylphenyl )-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene, the same method as in Example 1 was carried out to obtain the target compound with an isolation yield of 67%.

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Abstract

The invention relates to a method for preparing a 2-(2,2,2-trifluoroethyl)-3-aryl-2H-azirines compound. The structure of the 2-(2,2,2-trifluoroethyl)-3-aryl-2H-azirines compound is shown in figure 1, and a compound III and azidotrimethylsilane are adopted as raw materials to undergo two steps of reactions: (1) in the presence of alkali and additives, performing an azido reaction to obtain a compound which is shown in the general formula II; (2) preparing the compound which is shown in the general formula I through a denitrification cyclization reaction. The image is shown in the description. The method for synthesis of the 2-(2,2,2-trifluoroethyl)-3-aryl-2H-azirines compound is convenient and low in cost, and meanwhile the application of an expensive and unstable trifluoromethylation reagent is avoided.

Description

technical field [0001] The invention relates to a preparation method of 2-(2,2,2-trifluoroethyl)-3-aryl-2H-azyridine compound, which belongs to the field of compound preparation. Background technique [0002] 2H-Aziridine compounds are important intermediates in organic synthesis and important building blocks for the synthesis of nitrogen-containing compounds. For example, 2H-aziridine compounds can synthesize indole (Org. Lett.2010, 12, 3736.), pyrrole (Angew. Chem. Int. Ed. 2014, 53, 5653.), pyridine (Chem.Sci .2014, 5, 2347.), isoxazole (Org. Lett. 2009, 11, 2643.), etc. In addition to synthesizing other nitrogen-containing heterocyclic rings, in the field of pesticides and medicine, many active molecules (such as antiviral activity, cytotoxicity resistance) contain 2H-aziridine structures (Chem.Rev.2008,108,264 .; Med. Chem. Res. 2011, 20, 1042.). Therefore, the synthesis of 2H-aziridine compounds has great significance and value. [0003] It is well known that due t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D203/04
CPCC07D203/04
Inventor 周宇涵曲景平赵一龙刘建辉
Owner DALIAN UNIV OF TECH
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