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Method for catalyzed synthesis of quinoxaline compounds by yb/nay molecular sieve catalyst

A molecular sieve and catalyst technology, which is applied in the field of Yb/NaY molecular sieve catalyst to catalyze the synthesis of quinoxaline compounds, can solve problems such as higher requirements for synthesis conditions, and achieve the effects of simple synthesis method, high loading rate and uniform distribution

Inactive Publication Date: 2016-04-20
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with other synthesis methods using ionic liquids as catalysts, this invention has the characteristics of high catalytic activity and less catalyst consumption. However, due to the use of ionic liquids as catalysts, the synthesis conditions are relatively high.

Method used

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  • Method for catalyzed synthesis of quinoxaline compounds by yb/nay molecular sieve catalyst
  • Method for catalyzed synthesis of quinoxaline compounds by yb/nay molecular sieve catalyst
  • Method for catalyzed synthesis of quinoxaline compounds by yb/nay molecular sieve catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of Yb / NaY Molecular Sieve Catalyst

[0037] (1) Put the NaY molecular sieve powder in a polytetrafluoroethylene liner, add distilled water and magnets for electromagnetic stirring, and add dry YbCl while stirring 3 Powder, NaY and YbCl 3 The mass ratio is 1:1;

[0038] (2) Take out the magnet after stirring for 0.5h, wash it with distilled water, close the hydrothermal reaction kettle, and the filling degree of the polytetrafluoroethylene liner is 70%;

[0039] (3) Put the reactor into an oven, heat up to 180°C, take it out after 1 hour, and cool it with tap water;

[0040] (4) The mixture is centrifuged, and the liquid is evaporated to dryness to obtain incompletely reacted YbCl 3 , recovery, the solid is a loaded molecular sieve, and dried;

[0041] (5) Transfer the dried Yb / NaY molecular sieve to a crucible, heat up to 550°C in a muffle furnace at 10°C / min and then calcinate for 5h to obtain a Yb / NaY molecular sieve catalyst;

[0042] (6) Carry out ICP...

Embodiment 2

[0044] The Yb / NaY molecular sieve catalyst prepared in Example 1 was used to catalyze the synthesis of quinoxaline compounds from α-hydroxyketone and o-phenylenediamine.

[0045] 1mmol benzoin, 2mmol o-phenylenediamine, 0.35mmol morpholine and 0.05mmol Yb 3+ Place the Yb / NaY molecular sieve catalyst in a 25mL round-bottomed flask, add 5mL of acetic acid and a magneton, stir and reflux at 80°C for 4h. The obtained mixture is filtered, and the filter residue is a Yb / NaY molecular sieve catalyst, reclaimed, and the filtrate is separated by column chromatography to obtain a pure product, and the product structural formula is

[0046]

[0047] The yield was 93%, and the Yb / NaY molecular sieve catalyst was recovered and reused four times, and the yields were 91%, 93%, 92%, and 93%, respectively.

Embodiment 3

[0049]The Yb / NaY molecular sieve catalyst prepared in Example 1 was used to catalyze the synthesis of quinoxaline compounds from α-hydroxyketone and o-phenylenediamine.

[0050] 1 mmol 2-hydroxy-1,2-di-p-tolylethanolone, 2 mmol o-phenylenediamine, 0.35 mmol morpholine and 0.05 mmol Yb 3+ Place the Yb / NaY molecular sieve catalyst in a 25mL round-bottomed flask, add 5mL of acetic acid and a magneton, stir and reflux at 80°C for 4h. The obtained mixture is filtered, and the filter residue is a Yb / NaY molecular sieve catalyst, reclaimed, and the filtrate is separated by column chromatography to obtain a pure product, and the product structural formula is:

[0051]

[0052] The yield is 94%, and the Yb / NaY molecular sieve catalyst is recovered and reused once, and the yield is 92%.

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Abstract

The invention relates to a method for synthesizing a quinoxaline compound under catalysis of a Yb / NaY molecular sieve catalyst. The method specifically comprises the following steps of (a) mixing alpha-hydroxyketone, o-phenylenediamine, morpholine and the Yb / NaY molecular sieve catalyst, adding a solvent, and performing stirring and refluxing for 4 to 6 hours at 75 to 85 DEG C; (b) filtering the mixture obtained in the step (a), recycling a filter residue which is the Yb / NaY molecular sieve catalyst, and performing column chromatography separation on filtrate to obtain the quinoxaline compound. Compared with the prior art, a method for synthesizing the Yb / NaY molecular sieve catalyst is simple and metal load rate is high; the catalyst is high in thermal stability and easy to store and recycle; device characteristic detection shows that integrated molecular sieve pore passages and crystal structures of the catalyst are maintained; during condensation reaction between the alpha-hydroxyketone and the o-phenylenediamine under the catalysis of Yb / NaY, reaction conditions of are mild, simplicity in operation is ensured, the yield of a target product is 84 to 93 percent, and reduction in the cyclic catalysis efficiency of Yb / NaY is avoided.

Description

technical field [0001] The invention belongs to the field of industrial catalysis and organic compound synthesis, and relates to the application of a catalyst, in particular to a method for catalyzing and synthesizing quinoxaline compounds with a Yb / NaY molecular sieve catalyst. Background technique [0002] Quinoxaline and its derivatives are very important heterocyclic compounds. Due to their unique biological activities, they are often used in the synthesis of antibacterial, anticancer, anticonvulsant and antibad cell agents. In addition, they have a very wide range of applications in the preparation of fluorescent materials, organic semiconductors, chemical switches, dyes, and asymmetric catalysts. Therefore, the improvement of the synthesis method of quinoxaline has very important significance in pharmacy and various industrial productions. At present, most of the catalysts for the synthesis of quinoxalines using α-hydroxy ketones and o-phenylenediamine are homogeneous...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/42B01J29/08
CPCY02P20/584
Inventor 卫琳范丽岩
Owner TONGJI UNIV
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