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Method for synthesizing furan derivatives on basis of intermolecular ring-closure reaction

A technology of furan derivatives and closed-loop reaction, applied in the direction of organic chemistry, etc., can solve the problems such as difficulty in obtaining 1,4-diketone compounds, limited application, etc., and achieves the advantages of large-scale production, simple steps and high reaction yield. Effect

Active Publication Date: 2018-01-26
江西亚太科技发展有限公司
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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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  • Method for synthesizing furan derivatives on basis of intermolecular ring-closure reaction
  • Method for synthesizing furan derivatives on basis of intermolecular ring-closure reaction
  • Method for synthesizing furan derivatives on basis of intermolecular ring-closure reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～18

[0042] Following examples 1~18 react according to the best reaction condition after above-mentioned optimization:

Embodiment 1

[0044] Raw materials: acetophenone;

[0045] Target product:

[0046] Yield: 83%;

[0047] 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).

[0048] 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

[0050] Raw material: 2-bromoacetophenone;

[0051] Target product:

[0052] Yield: 62%;

[0053] 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).

[0054] 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 method for synthesizing furan derivatives on the basis of an intermolecular ring-closure reaction. According to the method, the furan derivatives are prepared from acetophenone compounds and dimethyl sulfoxide through a one-pot reaction in the presence of tetra-alkyl ammonium iodide catalyst and a potassium persulfate oxidizing agent. Varieties of the furan derivatives are enriched, more intermediates are provided for drug synthesis, raw materials are widely sourced, and the method adopts simple step and mild reaction conditions and is high in yield and beneficial toindustrial production.

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 potassium persulfate oxidation with acetophenone compound and dimethyl sulfoxide under the catalysis of tetraalkylammonium iodide , belonging to the field of pharmaceutical intermediate synthesis. 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 extract...

Claims

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Application Information

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IPC IPC(8): C07D307/64
Inventor 郭灿城胡雨群郭欣
Owner 江西亚太科技发展有限公司
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