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3,4,5-trisubstituted pyrazole compound and preparation method thereof

A compound and pyrazole technology, applied in the field of pyrazole compounds and their preparation, can solve problems such as difficulty in preparing 1,3-dione, and achieve the effects of high yield and single product structure

Inactive Publication Date: 2013-09-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the easy condensation of 1,3-diketones, there are some difficulties in the preparation of 1,3-diketones
Moreover, 1,3-diketones containing functional groups such as aldehyde groups, cyano groups, halogen groups, and ester groups are not suitable for the synthesis of pyrazole compounds by this method

Method used

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  • 3,4,5-trisubstituted pyrazole compound and preparation method thereof
  • 3,4,5-trisubstituted pyrazole compound and preparation method thereof
  • 3,4,5-trisubstituted pyrazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1, 3-benzoyl-4,5-diphenyl-1H-pyrazole (m1)

[0034] Add 42.4 mg (0.4 mmol) of benzaldehyde, 74.4 mg (0.4 mmol) of p-toluenesulfonyl hydrazide, and 99.6 mg (0.4 mmol) of 1,3-diphenyl-2-azido-2-propen-1-one to In the reaction flask, add 2.0 ml of DMF (N,N-dimethylformamide) and 0.08 g (2.0 mmol) of sodium hydroxide. After the addition, stir and react at 60°C for 2 hours, and detect the reaction by TLC (PE:EA= 4:1, namely petroleum ether: ethyl acetate = 4:1 volume ratio). After confirming the completion of the reaction, the reaction solution was extracted three times with 20*3 mL ethyl acetate, the organic layer (on the upper layer) was combined, washed three times with 30*3 mL saturated brine, and then dried with anhydrous sodium sulfate (about 2.0 g) for 30 Minutes, concentrated (concentrated with a rotary evaporator), column chromatography (PE:AE=6:1), the specific process parameters of the column chromatography are as follows:

[0035] A silica gel column is...

Embodiment 2

[0054] Example 2, 3-benzoyl-4-phenyl-5-(4-bromophenyl)-1H-pyrazole (m2)

[0055] Replace benzaldehyde with p-bromobenzaldehyde, the molar weight is constant, and all the other are equal to Example 1. 143.5 mg of the product 3-benzoyl-4-phenyl-5-(4-bromophenyl)-1H-pyrazole was obtained as a white solid, with a yield of 89%.

[0056] Its structural formula is:

[0057]

[0058] White solid; mp: 217.0 – 217.7 °C; 1 H NMR (500 MHz, CDCl 3 ) δ 11.08 (br s, 1H), 7.74 (d, J = 7.0 Hz, 2H), 7.43 – 7.41 (m, 3H), 7.25 – 7.21 (m, 4H), 7.18 – 7.17 (m, 3H), 7.10 (d, J = 6.1 Hz, 2H); 13 C NMR (125 MHz, CDCl 3 ) δ 188.12, 136.75, 135.08, 132.97, 131.91 131.56, 130.60, 129.98, 129.69, 128.42, 128.12, 127.61, 122.77; HRMS (ESI): m / z calcd for C 22 h 15 BrN 2 O [M+H] + : 403.0441, found: 403.0438.

Embodiment 3

[0059] Example 3, 3-benzoyl-4-phenyl-5-(3-bromophenyl)-1H-pyrazole (m3)

[0060] Replace benzaldehyde with m-bromobenzaldehyde, the molar weight is constant, and all the other are equal to Example 1. 137.7 mg of 3-benzoyl-4-phenyl-5-(3-bromophenyl)-1H-pyrazole was obtained as a white solid, with a yield of 85%.

[0061] Its structural formula is:

[0062]

[0063] White solid; mp: 155.5 – 156.5 °C; 1 H NMR (500 MHz, CDCl 3 ) δ 11.81 (br s, 1H), 7.73 (d, J = 6.4 Hz, 2H), 7.60 (s, 1H), 7.43 – 7.37 (m, 6H), 7.25 – 7.13 (m, 2H), 7.11 – 7.08 (m, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ 188.11, 136.64, 132.98, 131.41, 131.39, 131.03, 130.59, 130.09, 129.98, 128.39, 128.10, 127.63, 126.81, 123.02, 122.70 for CMS (zIcMS) : 22 h 15 BrN 2 O [M+H] + : 403.0441, found: 403.0442.

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Abstract

The invention discloses a 3,4,5-trisubstituted pyrazole compound. The 3,4,5-trisubstituted pyrazole compound is characterized in that the structural general formula of the compound is shown in the specification; and each of R1, R2 and R3 in the specification is a mono-substituted aromatic ring, a mono-substituted heteroaromatic ring, a poly-substituted aromatic ring, or a poly-substituted heteroaromatic ring. The invention also discloses a preparation method of the 3,4,5-trisubstituted pyrazole compound. The method sequentially comprises the following steps: 1, carrying out a one-pot reaction of an olefin nitrine compound, aldehyde and p-toluenesulfonohydrazide in the presence of a solvent and an alkali at 60-80DEG C for 1-2h; and 2, carrying out pumping filtration or column chromatography of a material obtained in step 1 to obtain the 3,4,5-trisubstituted pyrazole compound. The 3,4,5-trisubstituted pyrazole compound is an ideal antitumor lead compound, and antitumor medicines having novel structures are expected to be found through modifying the structure of the 3,4,5-trisubstituted pyrazole compound.

Description

technical field [0001] The invention belongs to a compound synthesis method, and mainly relates to pyrazole compounds and a preparation method thereof. Background technique [0002] Pyrazole compounds are an important class of heterocyclic compounds, which have broad development and application prospects in medicine and pesticides. Pyrazole compounds have biological activities such as antitumor, antibacterial, anti-inflammatory and hypoglycemic. Moreover, pyrazole derivatives, pyrazoline, are important intermediates for medicines and dyes. Therefore, pyrazole compounds play a pivotal role in both organic chemistry and medicinal chemistry. [0003] At present, the most important synthetic method of pyrazole compounds is: [0004] [0005] Using 1,3-diketone and hydrazine as raw materials, pyrazole compounds (Formula 1) were obtained through cyclization. But because 1,3-diketones are easy to condense, there are some difficulties in the preparation of 1,3-diketones. Mor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D401/04A61P35/00
Inventor 章国林倪航程陈斌辉俞永平
Owner ZHEJIANG UNIV
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