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Preparation of quinoxaline derivatives

A technology of quinoxaline derivatives, which is applied in the field of preparation of quinoxaline derivatives, can solve the problems of long reaction time, harsh reaction conditions, use of special instruments or devices, etc. The effect of mild conditions and less environmental pollution

Inactive Publication Date: 2010-12-08
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the above-mentioned prior art discloses various methods for preparing quinoxaline derivatives, these methods generally have one or more defects, such as: harsh reaction conditions; lower yield; reaction time is too long; side reactions Occurrence; The operation of the reaction and the separation of the products are cumbersome; Volatile and toxic organic solvents are commonly used; Expensive catalysts are used; Special instruments or devices are used, etc.
The most important shortcoming of existing synthetic method is that the catalyst recycling rate of price is very low, causes the cost of preparing quinoxaline derivative to increase

Method used

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  • Preparation of quinoxaline derivatives
  • Preparation of quinoxaline derivatives
  • Preparation of quinoxaline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add o-phenylenediamine (108mg, 1mmol), benzophenone (210mg, 1mmol), Amberlyst-15 (52mg, 0.24mmol) respectively in a 100mL three-neck round bottom flask equipped with a magnet, reflux condenser and thermometer , 24mL of water, started stirring and controlled the temperature at 25°C for 19 minutes, during which the reaction progress was monitored by TLC, and ethyl acetate-petroleum ether (v / v=1:5) was used as a developing solvent. After the reaction is finished, add 20 mL of ethyl acetate, stir well and then filter, so that the catalyst can be recovered. The organic layer in the above filtrate was collected, dried with anhydrous magnesium sulfate, filtered, and rotary evaporated to obtain the crude product of 2,3-diphenylquinoxaline. The crude product can be further purified with ethyl acetate-petroleum ether (v / v=1:6) as an eluent through a flash chromatography column to obtain pure 2,3-diphenylquinoxaline.

[0035] 2,3-Diphenyl-quinoxaline (the product in No. 1): m.p.1...

Embodiment 2

[0037] Add 4-methyl o-phenylenediamine (134mg, 1.1mmol), diphenyl ketone (210mg, 1mmol) and NKC-9 dry Hydrogen-catalyzed resin Styrene-DVB (76mg, 0.35mmol), 24mL water, start stirring and control the temperature at 50°C, react for 17 minutes, monitor the reaction progress with TLC during this period, use ethyl acetate-petroleum ether (v / v=1: 5) As a developing agent. After the reaction, add 20 mL of ethyl acetate, stir well and then filter, the catalyst can be recovered. The organic layer in the above filtrate was collected, dried with anhydrous magnesium sulfate, filtered, and rotary evaporated to obtain the crude product of 6-methyl-2,3-diphenylquinoxaline. The crude product was recrystallized from absolute ethanol to obtain pure 6-methyl-2,3-diphenylquinoxaline.

[0038] 6-methyl-2,3-diphenylquinoxaline (the product in No. 2): m.p.116-117°C; 1 HNMR (CDCl 3 , 300MHz) δ (ppm): 8.1 (d, 1H), 7.96 (s, 1H), 7.63 (dd, 1H), 7.5 (m, 4H), 7.35 (m, 6H), 2.6 (s, 3H); IR(KBr)υ max (...

Embodiment 3

[0040] Add 4-nitro-o-phenylenediamine (183mg, 1.2mmol), benzophenone (210mg, 1mmol), Amberlyst-15 ( 102mg, 0.47mmol) (for secondary use), 24mL water, start stirring and control the temperature at 65°C, react for 54 minutes, monitor the reaction progress with TLC during the reaction, use ethyl acetate-petroleum ether (v / v=1:5) as a developing agent. After the reaction, add 20 mL of ethyl acetate, stir well and then filter, the catalyst can be recovered. The organic layer in the above filtrate was collected, dried with anhydrous magnesium sulfate, filtered, and rotary evaporated to obtain the crude product of 6-nitro-2,3-diphenylquinoxaline. The crude product was further purified by flash chromatography using ethyl acetate-petroleum ether (v / v=1:6) as eluent to obtain pure 6-nitro-2,3-diphenylquinoxaline.

[0041] 6-nitro-2,3-diphenylquinoxaline (the product in No. 3): m.p.193-194°C; 1 HNMR (CDCl 3 , 300MHz) δ (ppm): 9.2 (d, 1H), 8.53 (dd, 1H), 8.39 (d, 1H), 7.6 (m, 4H), 7.4...

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Abstract

The invention discloses a preparation method of a quinoxaline derivative. The method is characterized by condensing an o-diamino compound with an o-dicarbonyl compound in a polar solvent in the presence of catalyst Amberlyst-15 or NKC-9 dry hydrogen catalyzed resin Styrene-DVB to prepare the quinoxaline derivative. The preparation method takes ordinary tap water instead of a toxic organic solventas the solvent for a condensation reaction to obtain the quinoxaline derivative with high yield and high content. The catalyst can be recovered and can be reused for at least three times in a condition of no loss of the catalytic activity, thus effectively reducing the production cost. The preparation method of the quinoxaline derivative has the advantages of simple process operation, no environment pollution, and is fit for large-scale industrialized production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a preparation method of quinoxaline derivatives. Background technique [0002] Quinoxaline derivatives are a very important class of nitrogen heterocyclic compounds. They have a wide range of biological activities, mainly including: antiviral; antibacterial; anti-inflammatory; antimicrobial; anthelmintic; anticancer; kinase inhibitor. Quinoxaline derivatives also form the basis of many insecticides, fungicides, herbicides, receptor antagonists. Although there are few reports on quinoxaline in nature, the synthetic quinoxaline unit is an important component of some antibiotics, such as echinazin and actinomycin, which have the ability to inhibit the growth of Gram-positive bacteria. effect. In addition, quinoxaline compounds have also been used in dyes, efficient electroluminescent materials, organic semiconductors, and DNA fragmentation reagents. In summary, quinoxalin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/42C07D241/06C07D409/14C07D471/04A61P31/04B01J31/08
CPCY02P20/584
Inventor 刘巨艳刘婧王佳迪
Owner TIANJIN NORMAL UNIVERSITY
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