A kind of synthetic method of the pyrazole compound of 4-iodination-n-arylation

A synthesis method and compound technology are applied in the synthesis field of pyrazole compounds, can solve problems such as restricted development and limited types of pyrazoles, and achieve the effects of high raw material economy, high product yield, and cheap and easy-to-obtain process raw materials

Active Publication Date: 2019-10-15
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the types of pyrazoles that can be synthesized by this method are limited, and the explosive nature of hydrazine compounds also limits its development.

Method used

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  • A kind of synthetic method of the pyrazole compound of 4-iodination-n-arylation
  • A kind of synthetic method of the pyrazole compound of 4-iodination-n-arylation

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Add 3,5-diethylpyrazole (10 mmol), iodobenzene acetate (15 mmol), AcOH (10 mmol), and dichloromethane 100 mL in sequence to a dry reaction tube, and react at room temperature for 10 hours. Potassium carbonate (10 mmol) was added under nitrogen protection, and the reaction was completed at room temperature for 24 hours. The corresponding product was obtained as a yellow liquid by column chromatography, and the yield was 74%. The name of the product is: 3,5-diethyl-4-iodo-1-phenyl-1-hydro-pyrazole. The structural formula is as follows:

[0019] ;

[0020] The proton nuclear magnetic resonance spectrum data of this product compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.48-7.41(m, 2H), 7.40-7.34 (m, 3H), 2.80-2.60 (m, 4H), 1.28 (t, J = 7.6 Hz, 3H), 1.09(t, J = 7.6 Hz, 3H); The carbon NMR data of the compound are as follows: 13 C NMR (100 MHz, CDCl 3 ) δ155.2, 145.8, 139.9, 129.0, 128.0, 125.2, 62.6, 21.8, 19.8, 13.2, 13.1; The high resolution mass spe...

Embodiment 2

[0022]

[0023] Add 3,5-diethylpyrazole (10 mmol), trivalent iodine compound (20 mmol), HClO in sequence to a dry reaction tube 4 (20 mmol), 100 mL of toluene, and the reaction at room temperature was completed for 20 hours. Triethylamine (20 mmol) was added under the protection of nitrogen, heated at 50°C for 10 hours, and the reaction was completed. The product was obtained by recrystallization from petroleum ether / ethyl acetate, and the yield was 65%. The name of the product is: 3,5-diethyl-4-iodo-1-(p-methylphenyl)-1hydropyrazole. The structural formula is as follows:

[0024] ; The proton nuclear magnetic resonance spectrum data of this product compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.25 (s, 4H), 2.73-2.57 (m, 4H), 2.40 (s, 3H), 1.28 (t, J = 7.6 Hz,3H), 1.09 (t, J = 7.6 Hz, 3H); The carbon NMR data of the compound are as follows: 13 C NMR (100 MHz, CDCl 3 ) δ 155.0, 145.9, 138.1, 137.5, 129.6, 125.3, 62.2, 21.8, 21.1, 19.9,13.3, 13.2; The hi...

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Abstract

The invention belongs to the field of organic synthetic chemistry, and particularly relates to a synthetic method of a 4- iodinated-N-arylated parazoles compound. The synthetic method comprises the following steps: mixing a parazoles compound, an iodonium compound, acid and an organic solvent, and reacting the mixture for several hours at normal temperature; and adding alkali on the premise of notcarrying out separation and purification, reacting for several hours at room temperature or while heating, and separating and purifying the obtained product by recrystallization or distillation or column chromatography on silica gel. The preparation method is green and effective. Compared with an existing method, the synthetic method has the advantages that raw materials of the process are low inprice and easy to obtain, reaction conditions are gentle, high temperature and other additives are not required, the economy of the raw materials is high, the product contains atomic iodine, and thus, follow-up modification and conversion are facilitated.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry, and in particular relates to a synthesis method of 4-iodide-N-arylation pyrazole compounds. Background technique [0002] The pyrazole structure is an important skeleton structure for the construction of biologically active compounds in the development of new drugs, and derivatives containing the pyrazole structure have a wide range of biological activities. As an important component, N-aryl substituted pyrazoles have always attracted the attention of researchers in the industry. Derivation on the basis of this structure, the obtained new compounds may exhibit different biological activities, which is beneficial to the discovery of pesticides or pharmaceutical leads. For example, the cyclooxygenase-2 (Celecoxib) inhibitor, a drug widely used to treat rheumatoid arthritis and osteoarthritis, is a non-steroidal drug containing a pyrazole core (Penning, T. D.; Talley, J. J.; Bertenshaw, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/16
Inventor 成佳佳路楠楠
Owner FUZHOU UNIV
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