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Method for synthesizing diaza-onium salt

A synthetic method, diazepine technology, applied in the direction of organic chemistry, can solve the problems of long reaction time, potential safety hazards, unfriendly environment, etc., and achieve the effect of simple operation, mild conditions, and environmental friendliness

Inactive Publication Date: 2009-02-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defective that this class method exists is: the use of organic solvent brings environment unfriendly (its volatility causes air pollution, and flammability causes potential safety hazard); Reaction time is long; Productive rate is not high

Method used

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  • Method for synthesizing diaza-onium salt
  • Method for synthesizing diaza-onium salt
  • Method for synthesizing diaza-onium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] Dicarbonyl compound 1a (5mmol, 500mg) and substituted o-phenylenediamine compound 2a (5.5mmol, 594mg) in pure water (6ml), add 0.005 equivalent of phosphotungstic acid (0.025mmol, 72mg) and stir at 25°C (ie room temperature) The reaction was carried out for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the organic layers were combined, the liquid was separated and the water layer was discarded; the organic layer was washed successively with saturated sodium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure. A crude product was obtained; the crude product was separated by column chromatography to obtain a light yellow solid 3a (518 mg, 72%).

[0020] Attached: 3a: 1 H NMR (CDCl 3 ): d 2.34 (s, 6H, CH 3 ), 2.81 (s, 2H, CH 2 ), 7.20-7.22 (m, 2H, Ph), 7.35-7.38 (m, 2H, Ph). 13 C NMR (CDCl 3 ): d 27.87, 43....

Embodiment 2

[0022]

[0023] Dicarbonyl compound 1a (5mmol, 500mg) and substituted o-phenylenediamine compound 2a (5.5mmol, 594mg) in pure water (6ml), add 0.01 equivalent of phosphotungstic acid (0.05mmol, 114mg) and stir at 25°C (ie, room temperature) React for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the organic layers were combined, the liquid was separated and the water layer was discarded; the organic layer was washed successively with saturated sodium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure. A crude product was obtained; the crude product was separated by column chromatography to obtain a light yellow solid 3a (662 mg, 92%).

Embodiment 3

[0025]

[0026] Dicarbonyl compound 1a (5mmol, 500mg) and substituted o-phenylenediamine compound 2a (5.5mmol, 594mg) in pure water (6ml), add 0.015 equivalent of phosphotungstic acid (0.075mmol, 216mg) and stir at 25°C (ie, room temperature) React for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the organic layers were combined, the liquid was separated and the water layer was discarded; the organic layer was washed successively with saturated sodium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure. A crude product was obtained; the crude product was separated by column chromatography to obtain a light yellow solid 3a (662 mg, 92%).

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Abstract

The invention relates to a method for synthesizing 2-nitrogen heterocyclic onium, aiming at providing a synthetic method which causes dicarbonyl compound and substituent o-Phenylenediamine to condense to obtain the 2-nitrogen heterocyclic onium by the catalysis of phosphotungstic acid in pure water. The method comprises the steps: the dicarbonyl compound and the substituent o-Phenylenediamine are mixed together at the room temperature, and the pure water is taken as solvent; the mixture is added with the phosphotungstic acid which is taken as catalyst to be stirred for reaction; after the reaction, organic horizons are extracted and merged by ethyl acetate; the organic horizons are sequentially washed by saturated sodium carbonate solution and saturated sodium chloride solution, dried, filtered decompressed and precipitated, so that the crude product is obtained and then separated by the column chromatography to obtain the pure product of 2-nitrogen heterocyclic onium. The product prepared by the invention is a type of important bioactivator and plays very important role in the synthesis and application of the medicine; the synthetic method has mild conditions and higher productive rate; as the pure water is taken as solvent, the method is environment-friendly; the reaction materials are easy to obtain and operate, thereby being suitable for laboratory preparation and industrial scale production.

Description

technical field [0001] The invention relates to a synthesis method of diazinium, in particular to a synthesis method of condensing a dicarbonyl compound and a substituted o-phenylenediamine compound to obtain a diazinium in pure water catalyzed by phosphotungstic acid. Background technique [0002] Existing methods for preparing diazinium include: carrying out hydrogen transfer N-heterocyclization (such as Tetrahedron Lett.2006,47,6899-6902) in the presence of a catalyst; and carrying out microwave reaction under phosphorus oxychloride reflux ( Such as Tetrahedron Lett.1995, 36, 6673-6674) and so on. The defects in this type of method are: the use of organic solvents is not friendly to the environment (its volatility causes air pollution, and its flammability causes safety hazards); the reaction time is long; and the yield is not high. Contents of the invention [0003] The purpose of the present invention is to overcome the deficiencies in the prior art, and provide a sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D243/14
Inventor 陈香佘进商志才吴军张培志
Owner ZHEJIANG UNIV
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