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Synthetic method of furan derivatives containing methylthio group

A technology of thiofuran and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of limited application, difficult to obtain 1,4-diketone compounds, etc., and achieves simple steps, is conducive to large-scale production, and mild reaction conditions. Effect

Active Publication Date: 2018-03-16
YUANJIANG HUALONG CATALYST TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is difficult to obtain by using 1,4-diketone compounds, which limits the application of this method

Method used

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  • Synthetic method of furan derivatives containing methylthio group
  • Synthetic method of furan derivatives containing methylthio group
  • Synthetic method of furan derivatives containing methylthio group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～18

[0041] Following examples 1~18 react according to the best reaction condition after above-mentioned optimization:

Embodiment 1

[0043] Raw materials: acetophenone;

[0044] Target product:

[0045] Yield: 83%;

[0046] 1 H NMR (400MHz, CDCl 3 ):δ8.05(dd,J=13.7,7.6Hz,1H),7.65–7.59(m,1H),7.53(t,J=7.1Hz,1H),7.48(t,J=7.1Hz,1H) ,7.43–7.37(m,1H),7.35(s,1H),2.48(s,1H).

[0047] 13 C NMR (101MHz, CDCl 3 ): δ181.8, 153.8, 150.3, 137.2, 132.6, 129.5, 129.3, 129.1, 128.7, 128.5, 126.5, 124.1, 118.1, 18.1.

Embodiment 2

[0049] Raw material: 2-bromoacetophenone;

[0050] Target product:

[0051] Yield: 62%;

[0052] 1 H NMR (400MHz, CDCl 3 ): δ7.67(t, J=7.7Hz, 1H), 7.52(d, J=7.3Hz, 1H), 7.36(ddd, J=26.3, 15.5, 7.6Hz, 2H), 7.22(s, 1H) ,2.34(s,1H).

[0053] 13 C NMR (100MHz, CDCl 3 ): δ182.4, 155.4, 150.8, 139.1, 133.4, 133.4, 132.3, 131.7, 131.3, 130.1, 129.4, 127.1, 127.1, 123.6, 123.4, 120.9, 120.0, 18.1.

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Abstract

The invention discloses a synthetic method of furan derivatives containing methylthio group. The synthetic method comprises: subjecting acetophenone compounds and dimethyl sulfoxide to one-pot reaction in the presence of an elemental iodine catalyst and potassium persulfate oxidant to obtain furan derivatives containing methylthio group. The synthetic method has the advantages that richer types offuran derivatives are provided, more intermediates are provided for drug synthesis, sources of materials are wide, the steps are simple, reaction conditions are mild, the yield is high, and industrial production is facilitated.

Description

technical field [0001] The present invention relates to a synthesis method of substituted furan, in particular to a method for generating furan derivatives by one-step reaction of acetophenone compound and dimethyl sulfoxide under the catalysis of elemental iodine through potassium persulfate oxidation, which belongs to the pharmaceutical intermediate body synthesis field. Background technique [0002] Furan derivatives are an important raw material or intermediate in organic or pharmaceutical synthesis. In the prior art, relatively complex furan derivative drugs often rely on extraction from natural plants. For example, Chinese patent (publication number: 101830871A) discloses a method for extracting furan derivatives from Trichosanthes mellifera fruit, specifically using ethanol to extract , chromatographic separation, and obtain furan derivative drugs that can be used to treat various diseases caused by the overactivation of the complement system. This method of extracti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/64
CPCC07D307/64
Inventor 郭灿城胡雨群郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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