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Diazole-pyrazolecarboxamide derivative and microwave hydrothermal synthesis method and application thereof

A kind of technology of derivatives and amides, applied in the application of such compounds, N--amide derivatives and the field of microwave hydrothermal synthesis

Inactive Publication Date: 2019-04-05
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this method is widely used in the synthesis of inorganic materials, but there are few reports on the application in organic synthesis. Experiments have proved that this method has the advantages of high yield, short time, simple operation, energy saving and environmental protection, and convenient post-processing. Large quantities can be prepared

Method used

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  • Diazole-pyrazolecarboxamide derivative and microwave hydrothermal synthesis method and application thereof
  • Diazole-pyrazolecarboxamide derivative and microwave hydrothermal synthesis method and application thereof
  • Diazole-pyrazolecarboxamide derivative and microwave hydrothermal synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1, N-[5-(5-methyl-[1,3,4]oxadiazol-2-yl)-2-cyclohexyl-2H-pyrazol-3-yl]-acetamide (Ⅲa 1 )Synthesis

[0069]

[0070] 5-Amino-1-cyclohexyl-1H-pyrazole-3-carbonitrile was synthesized from cyclohexylamine, 2,3-dicyano-propionic acid ethyl ester, ammonia water, etc. according to references: Chen Lianqing, Chen Guidi, Cheng Guosen, etc., 5 Synthesis and photophysical properties of -amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole derivatives[J].Journal of South Central University for Nationalities (Natural Science Edition), 2011,30(1); 5-12 self-made method.

[0071] (1) Take by weighing 15mmol 5-amino-1-cyclohexyl-1H-pyrazole-3-formonitrile with an analytical balance, add 30mL absolute ethanol thereto, shake and shake, then add 15mmol iron trichloride therein, Add a stirring magnet, stir and heat under reflux at 90°C for 14h, extract with ethyl acetate and water, and after rotary evaporation, perform silica gel column chromatography with ethyl acet...

Embodiment 2

[0075] Example 2, N-[5-(5-ethyl-[1,3,4]oxadiazol-2-yl)-2phenyl-2H-pyrazol-3-yl]-propionamide (Ⅲa 2 )Synthesis

[0076]

[0077] 5-Amino-1-phenyl-1H-pyrazole-3-carbonitrile was synthesized from aniline, 2,3-dicyano-propionic acid ethyl ester, ammonia water, etc. According to references: Chen Lianqing, Chen Guidi, Cheng Guosen, etc., 5-amino Synthesis and photophysical properties of -3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole derivatives[J].Journal of South Central University for Nationalities (Natural Science Edition),2011, 30(1); the method of 5-12 is self-made.

[0078] (1) Take by weighing 15mmol 5-amino-1-phenyl-1H-pyrazole-3-formonitrile with an analytical balance, add 30mL absolute ethanol thereto, shake and shake well, then add 15mmol iron trichloride therein, Add a stirring magnet, stir and heat under reflux at 90°C for 15 hours, then extract with ethyl acetate and water, and after rotary evaporation, use ethyl acetate and petroleum ether with a volum...

Embodiment 3

[0082] Example 3, N-[2-(4-hydroxy-phenyl-5-(5-propyl-[1,3,4]oxadiazol-2-yl)-2H-pyrazol-3-yl] -Butanamide (Ⅲa 3 )Synthesis

[0083]

[0084] 5-Amino-1-(4-hydroxy-phenyl)-1H-pyrazole-3-carbonitrile was synthesized from p-hydroxyaniline, 2,3-dicyano-propionic acid ethyl ester, ammonia water, etc. According to the reference: Chen Lianqing, Chen Guidi, Cheng Guosen et al. Synthesis and photophysical properties of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole derivatives[J].Journal of South Central University for Nationalities (Natural Science Edition), 2011, 30(1); self-made by the method of 5-12.

[0085] (1) Weigh 15mmol of 5-amino-1-phenyl-1H-pyrazole-3-carbonitrile with an analytical balance, add 30mL of n-propanol, shake and shake well, then add 15mmol of ferric chloride to it, add and stir Magneto, under stirring, heating at 85°C for 16h under reflux, then extracting with ethyl acetate and water, after rotary evaporation, use ethyl acetate and petrole...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a N-(5-[1,3,4]diazole-2-yl-2H-pyrazole-3-yl)-carboxamide derivative and a microwave hydrothermal synthesis method thereof, and further relates to application of the compound. A series of basic raw materials such as amine, 2,3-dicyan-opropionate, alcohol, acyl halide and the like are used for synthetizing of pyrazolecarbonitrile, pyrazolecarbonitrile is subjected to esterification, hydrazide reaction and amidation and reacts with a cyclization agent by the microwave hydrothermal synthesis method so as to obtainN-(5-[1,3,4]diazole-2-yl-2H-pyrazole-3-yl)-carboxamide derivative (including thiadiazole and oxadiazole). The derivative has good biological activity, can inhibit various bacterial stains, and has high activity in terms of bacterial resistance and insect killing; in terms of chemical structure, the derivative, according with the general formula, is synthetized, has great variety of active groups and excellent photo-physical properties, has multiple functions in the fields such as photoelectricity, medicines, pesticides, bacteriostat, diminish inflammation and virus protection, and accordinglyhas high development and application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an N-(5-[1,3,4]oxadiazol-2-yl-2H-pyrazol-3-yl)-amide derivative and its microwave hydrothermal The synthesis method also relates to the application of this type of compound. Background technique [0002] Thiadiazole compounds can play a variety of non-covalent bond interaction and coordination properties because they are easy to form hydrogen bonds and coordination bonds, and have anti-oxidation, anti-virus and anti-ulcer properties, especially for golden yellow Staphylococcus and Escherichia coli have obvious inhibitory effect. Pyrazole compounds can be used for sterilization, insecticide, weed control, anti-virus, promotion of plant growth and anti-cancer, etc., and have potential application value in the fields of pharmacy, medicine, and coordination chemistry. Pyrazole amide compounds have antibacterial, antiviral, anti-inflammatory and other uses in terms of biol...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D417/04C07D417/14A01N43/824A01P1/00A01P7/04C09K11/06
CPCA01N43/82C07D413/04C07D417/04C07D417/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1048C09K2211/1051
Inventor 陈连清王川川杜艳婷
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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