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Preparation of flavonoid derivatives by dehydration reaction between ethylenediamine compounds and baicalein under mild conditions

A technology for warm and dehydration reaction of baicalein, which is applied in the directions of organic chemistry, drug combination, antitumor drugs, etc., can solve the problems of difficult reuse of catalysts, increase production costs, heavy metal pollution, etc., and achieve easy industrialized production and reduced reaction times. Cycle and cost, low pollution effect

Active Publication Date: 2018-05-15
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst in the reaction process is difficult to reuse, and a large amount of alkali is consumed, which not only causes heavy metal pollution, but also increases production costs

Method used

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  • Preparation of flavonoid derivatives by dehydration reaction between ethylenediamine compounds and baicalein under mild conditions
  • Preparation of flavonoid derivatives by dehydration reaction between ethylenediamine compounds and baicalein under mild conditions
  • Preparation of flavonoid derivatives by dehydration reaction between ethylenediamine compounds and baicalein under mild conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1.06g of 1,2-diphenylethylenediamine and 1.35g of baicalein into a three-neck flask filled with 20mL of ethanol solution and stir. The system is heated up to 78°C, reacted for 20 hours, filtered while hot, and the filtrate is directly reconstituted. Crystallized to obtain 1.502 g of red crystals with a yield of 62%.

[0021] The product is detected by nuclear magnetic resonance and single crystal X-ray diffractometer, and the results are as shown in the figure, figure 1 for 1 H NMR (DMSO) spectrum, each peak belongs to complete, there is no obvious impurity peak in the figure, shows that the compound obtained is a pure phase. figure 2 It is the three-dimensional structure projection diagram of the product, and the three-dimensional structure of the product can be obtained intuitively. combine figure 1 , confirming that the high-purity target product 2,3,7-triphenyl-10-hydroxyl-1,2,3,4-tetrahydro-9H-pyrano[2,3-g]quinoxaline- 9-keto.

Embodiment 2

[0023] Add 1.06g of 1,2-diphenylethylenediamine and 1.35g of baicalein into a Erlenmeyer flask filled with 20mL of ethanol solution, shake it to fully dissolve it. Under indoor conditions, it was left standing in a fume hood, and after three days, 1.42 g of red crystals were obtained, with a yield of 59%.

[0024] The product was detected by nuclear magnetic resonance, and it was confirmed that the high-purity target product 2,3,7-triphenyl-10-hydroxyl-1,2,3,4-tetrahydro-9H-pyrano[2,3-g ] quinoxalin-9-one, consistent with the product obtained in Example 1.

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Abstract

The invention relates to a flavonoid derivative prepared through dehydration reaction between a quadrol compound and baicalein under the mild condition. 1, 2-diphenyl diaminoethane and the baicalein, as raw materials, are subjected to condensation backflow or room-temperature standing with the presence of low-boiling-point solvent to obtain a target product. The raw materials including the 1, 2-diphenyl diaminoethane and the baicalein both with medical value are subjected to 'solvent evaporation' or 'one-step' reaction to obtain the target product, namely the flavonoid derivative. Compared with common dehydration reactions between amines and phenolic hydroxyl groups or alcoholic hydroxyl groups, a compounding method, which can be applied with the absence of heavy metal catalysts, high temperature, high pressure and the like, has the advantages of simplicity, convenience, low cost, low pollution, high product purity and the like. Due to simplicity and convenience in operation, extremely mild reaction conditions and extremely low requirements on equipment selection, the compounding method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, relates to a research method of organic synthesis, and provides a new simple and mild dehydration synthesis reaction method. Background technique [0002] Typically, alkylation of amine and hydroxyl groups results in a carbon-nitrogen bond. It is reported that metal ruthenium or iridium complexes can be used as catalysts to make hydroxyl groups act on amides or sulfonamides through hydrogenation transfer to generate alkylated products. However, the catalyst in the reaction process is difficult to reuse, and a large amount of alkali is consumed, which not only causes heavy metal pollution, but also increases production costs. In the past decade, transition metal-catalyzed alkylation of alkylamines with hydroxyl groups has attracted great attention from researchers. With the increasing awareness of environmental protection, a green and efficient synthesis method of aminoalcohol is an urgent probl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052A61P31/12A61P29/00A61P35/00A61P31/00
CPCC07D491/052
Inventor 郭放付强
Owner LIAONING UNIVERSITY