Method for preparing multi-substituted benzo-[4,5]imidazo-[1,2-b] pyrazole derivative

A technology of pyrazole derivatives and imidazolo, which is applied in the field of preparation of multi-substituted benzo[4,5]imidazo[1,2-b]pyrazole derivatives, can solve the problem of irritating environment, many synthesis steps, Long reaction time and other problems, to achieve the effect of scientific and reasonable synthesis method, simple synthesis method and rapid reaction

Inactive Publication Date: 2016-08-10
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Using the above method to prepare polysubstituted benzimidazolopyrazole derivatives in the laboratory has obvious disadvantages: 1) There are many synthetic steps, complicated operation and long reaction time
2) The reagent sodium hydride used is strongly alkaline, and aryl chloride, triethylamine, and concentrated hydrochloric acid are irritating and environmentally unfriendly

Method used

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  • Method for preparing multi-substituted benzo-[4,5]imidazo-[1,2-b] pyrazole derivative
  • Method for preparing multi-substituted benzo-[4,5]imidazo-[1,2-b] pyrazole derivative
  • Method for preparing multi-substituted benzo-[4,5]imidazo-[1,2-b] pyrazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1) Preparation of benzimidazolopyrazole derivative 2a

[0028]

[0029] Add N-(2-bromophenyl)-5-phenyl-1H-pyrazol-3-amine 1a (94.25 mg, 0.3 mmol), catalyst cuprous iodide (11.43 mg, 0.06 mmol) into a 50 mL round bottom flask ), ligand 3-(imidazolidine-2-ylidene)pentane-2,4-dione (10.11 mg, 0.06 mmol), cesium carbonate (195.5 mg, 0.6 mmol) and DMSO (1 mL), which were placed Stir in an oil bath at 120°C. TLC detects that the reaction substrate disappears, and the reaction ends. After the reaction system was cooled to room temperature, 5 mL of water was added, and then extracted three times with 30 mL of ethyl acetate, the organic phases were combined, and extracted with anhydrous MgSO 4 Dry for 30 minutes, filter, and concentrate the filtrate with a rotary evaporator to obtain a crude product. The crude product was separated by silica gel column chromatography (eluent PE:EA=4:1), and concentrated by a rotary evaporator to obtain a pure product, which was confirmed t...

Embodiment 2

[0033] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0034]

[0035] Spectrum analysis data 2b:

[0036] 1 H NMR (DMSO-d 6 ,500MHz):δ11.52(s,1H),7.94–7.97(m,2H),7.76(d,J=7.9Hz,1H),7.42(d,J=8.0Hz,1H),7.23–7.29( m,3H),7.17–7.20(m,1H),6.32(s,1H); 13 C NMR (DMSO-d 6 ,125MHz): δ80.3,112.7,114.9,118.5( 2 J C – F =21.2Hz), 123.2, 126.3, 128.4, 130.4 ( 3 J C – F =8.5Hz), 133.8, 138.3, 148.0, 157.1, 164.8 ( 1 J C – F =241.9Hz); HRMS (ESI-TOF, [M+H] + ): calcd for C 15 h 11 FN 3 252.0937, found 252.0939.

Embodiment 3

[0038] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0039]

[0040] Spectrum analysis data 2c:

[0041] 1 H NMR (DMSO-d 6 ,500MHz): δ11.57(s,1H),7.78–7.98(m,2H),7.79(d,J=10.8Hz,1H),7.47–7.51(m,2H),7.45(d,J=8.4 Hz,1H),7.27–7.32(m,1H),7.19–7.23(m,1H),6.38(s,1H); 13 C NMR (DMSO-d 6 ,125MHz):δ77.9,110.2,112.4,120.6,123.9,125.8,127.6,129.0,132.6,133.6,135.8,145.4,154.2; HRMS(ESI-TOF,[M+H] + ): calcd for C 15 h 11 ClN 3 268.0642, found 268.0652.

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Abstract

The invention discloses a preparation method of polysubstituted benzo[4,5]imidazo[1,2-b]pyrazole derivatives, which belongs to the technical field of organic synthesis. The method is: in the reactor, add N-(2-bromoaryl)-5-aryl-1H-pyrazole-3-amine compound, cesium carbonate, catalyst cuprous iodide, ligand 3- (Imidazolidine-2-ylidene)pentane-2,4-dione, solvent DMSO, heated to the completion of the reaction, cooled the system to room temperature, added water, extracted three times with ethyl acetate, combined the organic phases, added anhydrous Dry over magnesium sulfate, filter, and concentrate the filtrate with a rotary evaporator to obtain a crude product, which is separated by silica gel column chromatography to obtain the product. The preparation method of the multi-substituted benzo[4,5]imidazo[1,2-b]pyrazole derivatives provided by the present invention is scientific and reasonable, the reaction is rapid, the synthesis method is simple, the yield is high, and the product is easy to purify, etc. . Its reaction equation is as follows:

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted benzo[4,5]imidazo[1,2-b]pyrazole derivatives. Background technique [0002] Benzimidazolopyrazole derivatives are an important class of heterocyclic compounds. Many benzimidazolopyrazoles and their derivatives have a wide range of physiological and pharmacological activities, such as anti-inflammatory, antibacterial and used for the treatment of cardiovascular disease, rheumatic heart disease and so on. [0003] Studies have found that benzimidazolopyrazole derivatives have a good inhibitory effect on the growth of bacteria (such as: Escherichia coli, Xanthomonas, etc.) and fungi (such as: Aspergillus fumigatus, Rhizoctonia solani, etc.). It is expected to become an effective drug for the treatment of plant bacterial diseases and fungal diseases, and has attracted widespread attention and research (Phosphorus, Sulfu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 文丽荣崔涛李明
Owner QINGDAO UNIV OF SCI & TECH
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