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Method for photocatalytic synthesis of 1,3,5-trisubstituted-2-pyrazole derivative

A technology of pyrazole derivatives and three substitutions, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc.

Inactive Publication Date: 2009-08-05
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are no patents and literature reports on the photocatalytic synthesis of 1,3,5-trisubstituted-2-pyrazole derivatives in an inert gas atmosphere

Method used

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  • Method for photocatalytic synthesis of 1,3,5-trisubstituted-2-pyrazole derivative
  • Method for photocatalytic synthesis of 1,3,5-trisubstituted-2-pyrazole derivative
  • Method for photocatalytic synthesis of 1,3,5-trisubstituted-2-pyrazole derivative

Examples

Experimental program
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Embodiment 1

[0047] Under argon protection, irradiate 1,3,5-triphenyl-2-pyrazoline with a 500W high-pressure mercury lamp (concentration is 10 -2 mol / l in 40ml CH 3 CN solution) with a catalytic amount of 2,2':6',2"-terpyridine divalent platinum complex (wherein R 1 for C 6 h 4 OCH 3 -4, R 2 is C≡CC 6 h 4 C≡CC 6 h 5 , R 3 , R 4 independent for H, R 5 for ClO 4 - , in 40ml CH 3 The concentration in CN solution is 10 -5 mol / l) acetonitrile solution, using a 480nm glass filter, monitor the reaction with thin layer chromatography, proton nuclear magnetic spectrum or fluorescence. After the reaction, evaporate the solvent, add ethyl acetate to extract, filter, spin the filtrate to obtain the product, and recover the insoluble catalyst. The product was identified as 1,3,5-triphenyl-2-pyrazole by H NMR and mass spectrometry.

Embodiment 2

[0049] Under argon protection, irradiate 1,3-diphenyl-5-p-methylphenyl-2-pyrazoline (concentration is 10-2mol / l, in 40ml methanol solution) and catalytic amount with 500W high-pressure mercury lamp The 2,2':6',2"-terpyridine divalent platinum complex (wherein R 1 for C 6 h 4 OCH 3 -4, R 2 is C≡CC 6 h 4 C≡CC 6 h 5 , R 3 , R 4 independent for H, R 5 for ClO 4 - , the concentration in 40ml methanol solution is 10 -5 mol / l) in methanol solution, irradiated with light with a wavelength of 450nm, and monitored the reaction with thin layer chromatography, nuclear magnetic hydrogen spectrum or fluorescence. After the reaction, evaporate the solvent, add ethyl acetate to extract, filter, spin the filtrate to obtain the product, and recover the insoluble catalyst. The product was identified as 1,3-diphenyl-5-p-methylphenyl-2-pyrazole by H NMR and mass spectrometry. The absorption spectrum of the reaction process is as figure 1 shown.

Embodiment 3

[0051] Under argon protection, compound 1,3-diphenyl-5-p-methylphenyl-2-pyrazoline was irradiated with a 500W high-pressure mercury lamp (concentration was 10 -2 mol / l, in 40ml methanol solution) with a catalytic amount of 2,2':6',2"-terpyridine divalent platinum complex (wherein R 1 for C 6 h 4 CH 3 -4, R 2 for Cl, R 3 , R 4 independent for H, R 5 for Cl - , the concentration in 40ml methanol solution is 10 -5 mol / l) of methanol solution, irradiated with light with a wavelength of 410nm, and monitored the reaction with thin layer chromatography, nuclear magnetic hydrogen spectrum or fluorescence. After the reaction, evaporate the solvent, add ethyl acetate to extract, filter, spin the filtrate to obtain the product, and recover the insoluble catalyst. The product was identified as 1,3-diphenyl-5-p-methylphenyl-2-pyrazole by H NMR and mass spectrometry.

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Abstract

The invention belongs to the field of catalysts, and particularly relates to 1,3,5-trisubstitution-2-pyrazole derivatives which are synthesized by the photochemical method. In the presence of a bivalent platinum complex catalyst with catalytic amount, and in the atmosphere of inert gas, an organic solvent containing the 1,3,5-trisubstitution-2-pyrazole derivatives is dissolved by the irradiation of visible light(lambda is more than 400nm and less than 570nm) so as to obtain the 1,3,5-trisubstitution-2-pyrazole derivatives. The method has the advantages of highly efficient reaction, easy separation and repeated use of the catalyst.

Description

technical field [0001] The invention belongs to the field of catalysts, in particular to synthesizing 1,3,5-trisubstituted-2-pyrazole derivatives by means of photochemistry. Background technique [0002] Pyrazole derivatives are an important class of heterocyclic compounds with unique physiological and pharmacological activities, such as: antibacterial, antifungal, enzyme inhibitors (MAP enzyme, DNA gyrase, DNA topoisomerase, etc.), herbicides , Insecticides, acaricides, etc., are widely used in the production of medicine and pesticides. As ligands, pyrazole derivatives coordinate with certain metals to form a new generation of "post-cene" metal catalysts for olefin polymerization. [0003] At present, the synthetic method of pyrazole derivative mainly contains three classes: (1) 1,3-diketone is cyclized with hydrazine or hydrazine derivative (Adv.Heterocycl.Chem.1966,6,347~429; CN 1401638A; CN 87103953A CN 1151159A; CN 1151733A; CN 1468854A; UP 5466823; UP 5521207); (2) 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06B01J31/22B01J31/30
Inventor 吴骊珠王登慧陈彬
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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