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Preparation method of 4-hydroxyl-3-substuted-thiazolane-2-ketone compound

A technology of ketone compounds and thiazolidine, which is applied in the field of medicine, can solve the problems of low product yield and achieve the effects of low cost, mild reaction conditions and high-efficiency synthesis

Inactive Publication Date: 2019-01-25
WUHAN POLYTECHNIC UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The main purpose of the present invention is to propose a preparation method of 4-hydroxyl-3-substituted-thiazolidin-2-ones, aiming at solving the problem of existing 4-hydroxyl-3-substituted-thiazolidin-2-ones The problem of low product yield in compound preparation method

Method used

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  • Preparation method of 4-hydroxyl-3-substuted-thiazolane-2-ketone compound
  • Preparation method of 4-hydroxyl-3-substuted-thiazolane-2-ketone compound
  • Preparation method of 4-hydroxyl-3-substuted-thiazolane-2-ketone compound

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[0029] In view of this, the present invention proposes a preparation method of 4-hydroxy-3-substituted-thiazolidin-2-one compounds. combine figure 1 The schematic flow diagram of an embodiment of the preparation method of the shown 4-hydroxyl-3-substituted-thiazolidin-2-one compound, the preparation of the 4-hydroxyl-3-substituted-thiazolidin-2-one compound The method includes the following steps:

[0030] Step S10, adding the acyl azide compound and 2,5-dihydroxy-1,4-dithiane into an organic solvent for ring closure reaction to obtain a reaction solution.

[0031] The synthetic route of the present invention is as follows:

[0032]

[0033] Wherein, "I" is the structural formula of the acyl azide compound, R 1 It is the No. 3 substituent in the 4-hydroxyl-3-substituted-thiazolidin-2-one compound to be prepared. In this embodiment, R 1 Preferred are phenyl, 4-methylphenyl, 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 4-cyanophenyl, 2-thiophene ...

Embodiment 1

[0048] Add 220.5 mg (1.5 mmol) of benzoyl azide to the reaction flask, then add 4 ml of acetonitrile and stir to dissolve at room temperature, then add 125.4 mg (0.825 mmol) of 2,5-dihydroxy-1,4 dithiane to In the reaction flask, add 4ml of acetonitrile, after the addition is complete, stir at 80°C, during which the reaction progress is detected by TLC (developing agent is petroleum ether-ethyl acetate (5:1, v / v)), when TLC detects the reaction When the result is that the benzoyl azide disappears, it means that the reaction is over.

[0049] After the reaction, the solid was removed by filtration, and extracted with ethyl acetate-water. After the obtained organic layer was washed and dried, the residual solvent was distilled off by a rotary evaporator to obtain a concentrate.

[0050] Select 10g of 200-300 mesh silica gel as the column chromatography, use petroleum ether: ethyl acetate=5:1 (v / v) as the eluent, set the flow rate as 3ml / min to the concentrated liquid column chro...

Embodiment 2

[0056] Add 220.5 mg (1.5 mmol) of benzoyl azide to the reaction flask, then add 3 ml of toluene and stir to dissolve at room temperature, then add 125.4 mg (0.825 mmol) of 2,5-dihydroxy-1,4 dithiane to In the reaction flask, add 3ml of toluene, after the addition is complete, stir at 80°C, during which the reaction progress is detected by TLC (the developer is petroleum ether-ethyl acetate (1:1, v / v)), when TLC detects the reaction When the result is that the benzoyl azide disappears, it means that the reaction is over.

[0057] After the reaction, the solid was removed by filtration, and extracted with ethyl acetate-water. After the obtained organic layer was washed and dried, the residual solvent was distilled off by a rotary evaporator to obtain a concentrate.

[0058] Select 10g of 200-300 mesh silica gel as the column chromatography, use petroleum ether:ethyl acetate=10:1 (v / v) as the eluent, set the flow rate to 3ml / min for the concentrated liquid column chromatography, ...

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Abstract

The invention discloses a preparation method of a 4-hydroxyl-3-substuted-thiazolane-2-ketone compound and relates to the technical field of medicine. The preparation method of the 4-hydroxyl-3-substuted-thiazolane-2-ketone compound includes the following steps of adding an acyl nitrine compound and 2,5-dyhydroxyl-1,4-dithiane into an organic solvent for a ring-closure reaction to obtain a reactionliquid; filtering the reaction liquid, obtaining a filtrate, removing impurities in the filtrate and then distilling the filtrate to obtain a concentrated liquid; conducting silica gel column chromatography on the concentrated liquid to obtain 4-hydroxyl-3-substuted-thiazolane-2-ketone. The provided preparation method can achieve efficient synthesis of 4-hydroxyl-3-substuted-thiazolane-2-ketone and increase the yield.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a preparation method of 4-hydroxy-3-substituted-thiazolidin-2-one compounds. Background technique [0002] Thiazolidinones, as a class of widespread five-membered heterocyclic compounds with broad-spectrum biological activities, have important applications in the fields of medicine, pesticides, and materials. Especially in recent years, studies have found that the thiazolidinone ring, as a very important structural unit, widely exists in many natural products and drugs, and is used for β-lactamase inhibitors, aldose reductase inhibitors, Pesticide fungicide, angiotensin receptor-II antagonist, insulin sensitizer. [0003] Due to the important application value of thiazolidinone compounds, their synthesis methods have been widely concerned. In the early days, people used haloacetaldehyde and thiocarbamic acid as raw materials to synthesize 3-methyl-4-hydroxy-thiazolidin-2-one. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/14C07D417/04
CPCC07D277/14C07D417/04
Inventor 王其林杨江科赵静国
Owner WUHAN POLYTECHNIC UNIVERSITY
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