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Synthetic method for thiocoumarin

A technology of thiocoumarin and synthesis method, applied in the field of thiocoumarin synthesis, can solve the problems of high cost, high toxicity, peculiar smell and the like, and achieves the effects of mild conditions and easy conditions

Active Publication Date: 2018-08-10
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In summary, most of the currently developed methods for constructing C-S bonds have some obvious limitations, such as unavailable raw materials, high cost, odor, high toxicity, and low yield.
The latest research shows that C-4 amino substituted coumarin has significant anticancer activity, and it is expected to develop a new anticancer drug. However, the synthesis of thio C-4 amino coumarin has not been reported, so It is of great significance to develop a method for the efficient synthesis of thio-C-4 amino-substituted coumarin using Bunte salt for the screening of anticancer drugs

Method used

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  • Synthetic method for thiocoumarin
  • Synthetic method for thiocoumarin
  • Synthetic method for thiocoumarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] At room temperature, add simple iodine (0.04 mmol), aminocoumarin (0.2 mmol), S-benzyl thiosulfate O-sodium into a 25 ml Schlenk tube equipped with a magnetic stirrer Salt (0.3 mmol), 2 mL DMSO was added under air, and the reaction tube was placed in an oil bath at 60° C. and stirred for 24 h. After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 53 mg of the corresponding target product with a yield of 74% .

[0031] The chemical reaction formula is:

[0032]

[0033] The obtained product nuclear magnetic spectrum data are:

[0034] 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.72(s,1H),7.40-7.37(m,1H),7.30(d,1H...

Embodiment 2

[0039] At room temperature, add simple iodine (0.04 mmol), aminocoumarin (0.2 mmol), S-4-methylbenzyl thiosulfate into a 25 ml Schlenk tube equipped with a magnetic stirrer Ester O-sodium salt (0.3 mmol), 2 mL DMSO was added under air, and the reaction tube was placed in an oil bath at 60°C and stirred for 24 h. After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 67 mg of the corresponding target product with a yield of 90% .

[0040] The chemical reaction formula is:

[0041]

[0042] The obtained product nuclear magnetic spectrum data are:

[0043] 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.84(s,1H),7.40(s,1H),7....

Embodiment 3

[0047] At room temperature, add simple iodine (0.04 mmol), aminocoumarin (0.2 mmol), S-phenylethyl thiosulfate O- Sodium salt (0.3 mmol), 2 mL DMSO was added under air, and the reaction tube was placed in an oil bath at 60° C. and stirred for 24 h. After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain 62 mg of the corresponding target product with a yield of 83% .

[0048] The chemical reaction formula is:

[0049]

[0050] The obtained product nuclear magnetic spectrum data are:

[0051] 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.74(s,1H),7.45-7.42(m,1H),7.33(t,3H,J

[0052] =15.0Hz), 7.21-7.14(m, 7H), 7.01(d, 2H, ...

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PUM

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Abstract

The invention discloses a synthetic method for thiocoumarin, and relates to the field of organic synthesis. The synthetic method for thiocoumarin comprises the following steps: taking C-4-positioni amino substituted coumarin and organic thiosulfate as raw materials; and reacting for (18-30) h at the temperature of (40-100) DEG C through iodine catalysis to obtain a C-3-position sulfur substitutedcoumarin compound. The invention provides a novel method for synthesizing an amino coumarins derivative with potential anti-cancer activity. Raw materials are economical and easily obtained, reactionconditions are green, low-toxicity and odorless, and the synthetic method for thiocoumarin has the advantages of gentle reaction conditions, low cost, small environmental pollution, high yield and thelike.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing thiocoumarin. Background technique [0002] Coumarin is an important natural product with a variety of biological activities, which is widely used in the field of medicinal chemistry. At the same time, this kind of compound also has good optical properties, and has also received great attention in the field of organic materials. [0003] On the other hand, the functional group thioether is widely found in pharmaceuticals and agrochemicals. Through sulfuration reactions, sulfur-containing functional groups are added to bioactive molecules, which significantly alters their pharmacological activity. Thus, the construction of C–S bonds has attracted great interest among medicinal and synthetic organic chemists over the past few decades. Literature research shows that the construction of C-S bonds is usually prepared by cross-coupling halogenated aromatic h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/12C07D311/18
CPCC07D311/12C07D311/18
Inventor 杨道山魏伟
Owner QINGDAO UNIV OF SCI & TECH
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