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Method and application of ultrasonic one-pot preparation of pyrazole sulfonamide sodium, potassium, calcium metal complexes

A technology of metal complexes and pyrazole sulfonamides, applied in potassium organic compounds, sodium organic compounds, calcium organic compounds, etc., to achieve high activity, increased reaction yield, and excellent biological activity

Active Publication Date: 2018-11-20
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Metal complexes synthesized by introducing main group metal ions such as sodium, potassium, and calcium into sulfonamide structures with insecticidal and antibacterial activities have not been discovered so far

Method used

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  • Method and application of ultrasonic one-pot preparation of pyrazole sulfonamide sodium, potassium, calcium metal complexes
  • Method and application of ultrasonic one-pot preparation of pyrazole sulfonamide sodium, potassium, calcium metal complexes
  • Method and application of ultrasonic one-pot preparation of pyrazole sulfonamide sodium, potassium, calcium metal complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the synthesis of sodium complex

[0039]

[0040] Add 1 mmol of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole to the flask, followed by 25 mL of acetic acid Ethyl ester, then slowly add 1.5mmol NaH, continue to stir for 0.5h after adding, then dropwise add 1mmol p-toluenesulfonyl chloride, put it into an ultrasonic reactor for reaction, adjust the power of the ultrasonic reactor to 100W, after 1h, extract with water, The inorganic salts were removed, the organic layer was collected, dried overnight by adding anhydrous magnesium sulfate, and a white powder product was obtained by column chromatography. Yield: 86.3%. 1 H-NMR (400MHz, DMSO-d 6 )4.01(q,2H),1.97(s,3H),1.16(t,3H),2.66~2.71(q,2H),1.04~1.08(t,3H); IRν(cm -1 ):2252(ν C≡N ), elemental analysis: according to the theoretical structural formula C 23 h 18 Cl 2 f 6 N 4 NaO 5 S 2 , Calculated: C, 39.38; H, 2.44; N, 7.99%, found: C, 39.79; H, 2.66;...

Embodiment 2

[0052] Embodiment 2, the synthesis of potassium complex

[0053]

[0054] Add 1 mmol of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole to the flask, followed by 25 mL of acetic acid Ethyl ester, then slowly add 1.5mmol KOH, continue to stir for 0.5h after the addition, then dropwise add 1mmol p-toluenesulfonyl chloride, put it into an ultrasonic reactor for reaction, adjust the power of the ultrasonic reactor to 100W, and extract it with water after 2h of reaction , remove inorganic salts, collect the organic layer, add anhydrous magnesium sulfate to dry overnight, and obtain a white powder product by column chromatography. Yield: 85.3%. 1 H-NMR (400MHz, DMSO-d 6 )7.90~7.93(m,4H),4.01(q,2H),1.97(s,3H),1.16(t,3H),2.66~2.71(q,2H),1.04~1.08(t,3H); IRν (cm -1 ):2252(ν C≡N ), elemental analysis: according to the theoretical structural formula C 19 h 9 Cl 2 f 6 KN 4 o 3 S 2 , Calculated: C, 37.22; H, 2.03; N, 8.68%, Found: C...

Embodiment 3

[0065] Embodiment 3, the synthesis of calcium complex

[0066] Add 1 mmol of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole to the flask, followed by 20 mL of acetic acid Ethyl ester and 5mL water, then slowly add 1.5mmol Ca(OH) 2 After the addition, continue to stir for 0.5h, then dropwise add 1mmol p-toluenesulfonyl chloride, put it into an ultrasonic reactor for reaction, adjust the power of the ultrasonic reactor to 100W, and after reacting for 2h, extract with water to remove inorganic salts and collect the organic layer. Anhydrous magnesium sulfate was added to dry overnight, and a white powder product was obtained by column chromatography. Yield: 79.6%. 1 H-NMR (400MHz, DMSO-d 6 )4.02(q,2H),1.98(s,3H),1.17(t,3H),2.62~2.75(q,2H),1.06~1.01(t,3H); IRν(cm -1 ):2254(ν C≡N ). Elemental analysis: according to the theoretical structural formula C 46 h 46 CaCl 4 f 12 N 8 o 16 S 4 , Calculated: C, 36.25; H, 3.72; N, 6.26%, f...

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Abstract

The invention belongs to the technical field of organic synthesis, and concretely discloses a method for preparing pyrazole sulfamide type sodium, potassium and calcium metal complexes by an ultrasonic wave one-pot method and application. Pyrazolone ring amidogen is subjected to structure modification and solvent participation; a series of pyrazole sulfamide type sodium, potassium and calcium metal complexes are synthesized by the ultrasonic wave one-pot method. The metal coordination modes of sodium, potassium, calcium and the like are diversified; the coordination with nitrogen atoms and oxygen atoms on sulfamide is realized; the coordination with oxygen atoms on a solvent can also be realized; metal on the potassium complex can also be coordinated with halogen atoms on substitutional groups; the synthetized sulfamide type metal complexes based on a pyrazole framework have excellent biological activity; particularly, high activity is shown in the insect killing and antibiosis aspects, so that the synthetized sulfamide type metal complexes based on the pyrazole framework have great research and development and application values.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method and application for preparing pyrazole sulfonamide sodium, potassium and calcium metal complexes by an ultrasonic one-pot method. Background technique [0002] Looking at the metabolic process of living organisms, we can know that metal ions such as potassium, calcium, and sodium play a vital role in the process of life activities. For example, the sodium ion channels and potassium pumps running through the cell membrane can affect the material energy of living organisms. Various life activities such as metabolism and transmission of nerve signals, and for example, in some living organisms, cellulase encounters Mn 2+ 、Cu 2+ 、Cr 2+ and Mo 2+ Its activity is inhibited when four kinds of metal ions encounter Fe 2+ 、Se 2+ , Zn 2+ The biological activity of the three ions is significantly enhanced. It is well known that there are various balance mechanisms an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/04C07F1/06C07F3/04A01N43/56A01P1/00A01P7/04
CPCA01N43/56C07F1/04C07F1/06C07F3/04
Inventor 陈连清黄裕峰万子露
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES