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4-Chromanone compound containing trifluoromethyl and preparation method of 4-Chromanone compound

A technology for chroman and ketone compounds, which is applied in the field of chroman-4-one compounds and their preparation, and achieves the effects of mild reaction conditions and simple operation

Active Publication Date: 2019-03-01
XINYANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the reported synthetic methods of chroman-4-ones are mainly through Michael addition (references: J.Chem.Soc.1935,866; Org.Biomol.Chem.2011,9, 6930; Org.Lett.2011,13,4526; Chem.Commun.2012,48,11796; Angew.Chem.Int.Ed.2015,54,13302; ChemCatChem.2017,9,465) and intramolecular dehydration condensation (reference Literature: J.Org.Chem.1961,26,4941; Eur.J.Org.Chem.2003,4575; Org.Lett.2012,14,2710; Molecules2015,20,43; Tetrahedron Lett.2016,57,3841 ) to obtain, but for the synthesis of trifluoromethylated chroman-4-one compounds, there is no report yet

Method used

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  • 4-Chromanone compound containing trifluoromethyl and preparation method of 4-Chromanone compound
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  • 4-Chromanone compound containing trifluoromethyl and preparation method of 4-Chromanone compound

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preparation example Construction

[0021] The described a trifluoromethyl-containing chroman-4-one compound and its preparation method comprise the following steps:

[0022] Disperse the aldehyde compound of structure (I), the trifluoromethyl reagent of structure (II) and the oxidizing agent in a solvent, and heat and stir to obtain trifluoromethylated chroman with structure (III) -4-Kone compounds:

[0023]

[0024] The specific structure of III is:

[0025]

[0026] Described oxidizing agent is potassium persulfate, sodium persulfate or ammonium persulfate;

[0027] The solvent is a mixture of acetonitrile, ethanol, isopropanol, N,N-dimethylformamide, acetone, 1,4-dioxane, dimethyl sulfoxide, ethyl acetate or dichloromethane and water ;

[0028] The molar ratio of the aldehyde compound to the trifluoromethyl reagent is 1:1-1:1.6;

[0029] The molar ratio of the aldehyde compound to the oxidizing agent is 1:1-1:3;

[0030] Described reaction temperature is 50 ℃-100 ℃;

[0031] The reaction time is ...

Embodiment 1

[0033] In a clean and dry 20mL Schlenk pressure-resistant reaction tube, add 1mmol allyl salicylaldehyde, 1.5mmol sodium trifluoromethanesulfinate, and 3mmol potassium persulfate successively, then add 1.5mL acetonitrile and 2.5mL water as solvents, The reaction tube was sealed and placed in an oil bath at 70° C. to react for 8 hours. After the reaction was finished, ethyl acetate was added to extract the reaction mixture, the organic phase was spin-dried by a rotary evaporator, and the residue obtained was separated by a silica gel column with petroleum ether and ethyl acetate as eluents, and the target product obtained was Colorless oily liquid, yield 62%.

[0034] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the NMR fluorine spectrum is shown as Figure 1b As shown, the carbon NMR spectrum is as Figure 1c shown. It can be confirmed from the spectrum that the obtained product is the target c...

Embodiment 2

[0036] Add 1mmol 4-methoxyallyl salicylaldehyde, 1.5mmol sodium trifluoromethanesulfinate, 2.5mmol potassium persulfate, 1.5mL acetonitrile and 2.5 mL of water was used as a solvent, and the reaction tube was sealed and placed in an oil bath at 80° C. for 8 hours to react. After the reaction was finished, ethyl acetate was added to extract the reaction mixture, the organic phase was spin-dried by a rotary evaporator, and the residue obtained was separated by a silica gel column with petroleum ether and ethyl acetate as eluents, and the target product obtained was White solid, 38% yield.

[0037] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 2a As shown, the NMR fluorine spectrum is shown as Figure 2b As shown, the carbon NMR spectrum is as Figure 2c shown. It can be confirmed from the spectrum that the obtained product is the target compound 2b.

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Abstract

The invention provides a 4-Chromanone target compound (III) containing trifluoromethyl and a preparation method of the 4-Chromanone target compound (III), wherein the 4-Chromanone target compound (III) is obtained in the modes that an allylsalicylaldehyde (I) compound serves as a reaction starting raw material, sodium triflate (II) serves as a trifluoromethyl source, persulfate serves as an oxidant, and the trifluoromethyl and allylsalicylaldehyde generate free radical addition, free radical cyclization and an oxidation reaction. The reaction condition involved in the method is mild, operationis easy, product diversity is achieved, and gram-scale production can be achieved.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a trifluoromethyl-containing chroman-4-one compound and a preparation method thereof. Background technique [0002] Chromone-4-one compounds are an important class of organic chemical raw materials, and have shown broad application prospects in many fields such as organic synthesis, polymers, synthetic drugs, and pesticides. Compounds containing trifluoromethyl groups have unique biological and chemical activities. Therefore, the trifluoromethyl-containing chroman-4-one compound will possess the properties and characteristics of both the chroman-4-one compound and the trifluoromethyl-containing compound. So far, the reported synthetic method of chroman-4-ones is mainly through Michael addition (references: J.Chem.Soc.1935,866; Org.Biomol.Chem.2011,9, 6930; Org.Lett.2011,13,4526; Chem.Commun.2012,48,11796; Angew.Chem.Int.Ed.2015,54,13302; ChemCatChem.2017,9,465) and intramolecu...

Claims

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Application Information

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IPC IPC(8): C07D311/22C07D311/92
CPCC07D311/22C07D311/92
Inventor 唐林杨禛常雪萍焦景超周秋菊郑凌云
Owner XINYANG NORMAL UNIVERSITY
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