Preparation method of 3-substituted-thiazol-2(3H)-one compound

A technology of ketone compounds and compounds, which is applied in the field of preparation of 3-substituted-thiazol-2-one compounds, can solve the problems of poor applicability of different functional groups, use of precious metal reagents, and difficult acquisition of raw materials, etc. Easy handling and high productivity

Inactive Publication Date: 2018-11-06
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although there are many reports on the synthesis of thiazolone compounds, the known synthetic methods still have problems such as difficult acquisition of raw materials, low product yield, poor applicability to different functional groups, and the use of precious metal reagents.

Method used

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  • Preparation method of 3-substituted-thiazol-2(3H)-one compound
  • Preparation method of 3-substituted-thiazol-2(3H)-one compound
  • Preparation method of 3-substituted-thiazol-2(3H)-one compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0039] Example 1-1, 3-phenyl-thiazol-2(3H)-one (m1)

[0040] 1) Add 220.5 mg (1.5 mmol) of benzoyl azide and 125.4 mg (0.825 mmol) of 2,5-dihydroxy-1,4-dithiane into the tube (sealed tube), and then add 7.5 ml of solvent- -Acetonitrile, after the addition, stirred and reacted at 80°C for 21h, and detected the reaction by TLC (petroleum ether:ethyl acetate=5:1 volume ratio), at this time, the result of the TLC detection reaction was that the benzoyl azide disappeared.

[0041] 2), add mass concentration 40% sulfuric acid aqueous solution (the molar weight of sulfuric acid is 0.375mmol) to the resultant of step 1), stir at room temperature for one hour, TLC monitoring (petroleum ether: ethyl acetate=3:1 volume ratio) step 1) The obtained 4-hydroxy-3-phenylthiazolidin-2-one disappeared, indicating that the reaction had ended.

[0042] That is, sulfuric acid: benzoyl azide = 25 mol%.

[0043] After the reaction was finished, the solid was removed by filtration, the filtrate was ...

Embodiment 1-2

[0050] Embodiment 1-2, replace acetonitrile with dioxane, the volume is constant, all the other are the same as embodiment 1-1. 218 mg of 3-phenylthiazol-2(3H)-one was obtained as light yellow oily product, and the yield was 80%.

Embodiment 2

[0062] Example 2, 3-(4-fluoro-phenyl)thiazol-2(3H)-one (m2)

[0063] Use p-fluorobenzoyl azide instead of benzoyl azide, the molar weight remains unchanged, and the rest is the same as in Example 1-1. 219.3 mg of the product 3-(4-fluoro-phenyl)thiazol-2(3H)-one was obtained as a white powder, with a yield of 75%.

[0064] Its structural formula is:

[0065] White powder 1 H NMR (500MHz, DMSO-d 6 )δ7.57(dd, J=8.5,5Hz,2H),7.35(t,J=9.0Hz,2H),7.30(d,J=5.5Hz,1H),6.65(d,J=5.5Hz,1H ). 13 C NMR (125MHz, DMSO-d 6 ) 170.26, 161.85, 159.9 132.98 (d, 3 J C,F =10Hz), 126.80(d, 2 J C,F =35Hz), 116.13(d, 1 J C,F =95Hz), 102.03HRMS(ESI):m / z calcd for C 9 h 6 FNOS[M+H]+:196.0232,found:196.0229.

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Abstract

The invention discloses a preparation method of a 3-substituted-thiazol-2(3H)-one compound. The preparation method sequentially comprises the following steps: performing a reaction on an acyl azide compound and 2,5-dihydroxy-1,4-dithiane in a solvent at 80 DEG C plus or minus 5 DEG C for 18-21h; adding an aqueous sulfuric acid solution into an obtained reaction solution, reacting while stirring, and then filtering to remove a solid; performing a rotary evaporation on a filtrate to remove the solvent, then adding water, extracting by using ethyl acetate, washing an obtained organic layer by using a saturated salt solution, drying, then performing a rotary evaporation to remove the ethyl acetate, and performing silica gel column chromatography on an obtained concentrate to obtain the 3-substituted-thiazol-2(3H)-one compound. By the preparation method, the condition is mild, the yield is high, the posttreatment is convenient, the pollution is less, used raw materials are easy to obtain, and a simple and easily-implemented method is provided for efficiently synthesizing the 3-substituted-thiazol-2(3H)-one compound.

Description

technical field [0001] The invention belongs to a compound synthesis method, and mainly relates to a preparation method of a 3-substituted-thiazol-2(3H)-one compound. Background technique [0002] Thiazolones, as a class of widespread five-membered heterocyclic compounds with broad-spectrum biological activity, 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, such as inhibitors of lactamase and aldose reductase, agrochemical fungicides, and angiotensin-II receptor antagonists, rosiglitazone, etc. , is used for β-lactamase inhibitors, aldose reductase inhibitors, pesticide fungicides, angiotensin receptor-II antagonists, and insulin sensitizers. [0003] Due to the important application value of thiazolone compounds, their synthetic methods have been widely concerned: [0004] 1),...

Claims

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Application Information

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IPC IPC(8): C07D277/34C07D417/04
CPCC07D277/34C07D417/04
Inventor 章国林王其林竺越俞永平
Owner ZHEJIANG UNIV
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