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A kind of synthetic method of 3-benzenesulfonyl coumarin compound

A technology of coumarins and synthetic methods, applied in the direction of organic chemistry, can solve the problems of high cost, long reaction time, complex reaction system, etc., and achieve the effect of mild conditions, simple method, and environmental friendliness

Inactive Publication Date: 2019-10-08
QINGDAO AGRI UNIV
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Problems solved by technology

[0003] However, when adopting the above method to synthesize coumarin compounds, the reaction system used is relatively complicated, not only the reaction time is longer, the yield is low, but also the raw materials are difficult to synthesize and the cost is high

Method used

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  • A kind of synthetic method of 3-benzenesulfonyl coumarin compound
  • A kind of synthetic method of 3-benzenesulfonyl coumarin compound
  • A kind of synthetic method of 3-benzenesulfonyl coumarin compound

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preparation example Construction

[0023] The embodiments of the present invention provide a method for synthesizing 3-benzenesulfonyl coumarin compounds, comprising the following steps:

[0024] S1: respectively add coumarin compounds and sodium benzene sulfinate compounds into the reaction flask, and react at 55°C-70°C for 8-10 hours under the action of iodine and dimethyl sulfoxide.

[0025] In this step, 3-benzenesulfonyl coumarin compounds are synthesized by using coumarin compounds and sodium benzene sulfinate compounds. In this step, sodium benzene sulfinate reacts with iodine to generate benzene sulfinate The acyl radical, and then the benzenesulfinyl radical undergoes an addition reaction to the coumarin, and finally the hydrogen atom is removed under the action of iodine to generate the target product. It can be understood that the temperature and reaction time set in this step can be selected by those skilled in the art according to the actual reaction conditions, as long as it is ensured that the re...

Embodiment 1

[0042] Add coumarin and sodium p-toluene sulfinate to the reaction flask respectively, and under the action of iodine and dimethyl sulfoxide, react for 8-10 hours at a temperature of 55°C-70°C; after the reaction is completed, carry out Chromatography gave white crystals, 3-Tosyl-2H-chromen-2-one (1):

[0043]

[0044] The above-mentioned white crystalline powder was analyzed by nuclear magnetic spectrum, and the data were as follows:

[0045] 1 H NMR (400MHz, CDCl 3 )δ: 2.46(s, 3H), 7.35(d, J=8.0Hz, 3H), 7.37(td, J=7.7, 1.0Hz, 1H), 7.68-7.72(m, 2H), 8.03(dd, J =6.5,1.5Hz,2H),8.77(s,1H);

[0046] 13C NMR (100MHz, CDCl 3 )d: 21.8, 117.1, 117.5, 125.5, 128.7, 129.3, 129.7, 130.3, 135.2, 135.4, 145.6, 147.1, 154.8, 155.6;

[0047] After identification, the spectral data corresponded to the structural formula, and it was proved that the synthesized product was 3-toluenesulfonyl-2H-chromen-2-one with a yield of 80%.

Embodiment 2

[0049] Add coumarin and sodium benzene sulfinate to the reaction flask respectively, under the action of iodine and dimethyl sulfoxide, react at 55 ℃-70 ℃ temperature for 8-10 hours; after the reaction is completed, carry out chromatographic separation, White crystals were obtained, namely 3-benzenesulfonyl-2H-chromen-2-one (2):

[0050]

[0051] The above-mentioned white crystalline powder was analyzed by nuclear magnetic spectrum, and the data were as follows:

[0052] 1 H NMR (400MHz, CDCl 3 )δ: 7.38(d, J=8.5Hz, 1H), 7.42(t, J=8.0Hz, 1H), 7.56(t, J=7.5Hz, 2H), 7.64-7.69(m, 1H), 7.73( t, J=7.5Hz, 2H), 8.14 (d, J=8.5Hz, 2H), 8.82 (s, 1H);

[0053] 13 C NMR (100MHz, CDCl 3 )d: 117.1, 117.2, 125.6, 128.4, 129.2, 129.4, 130.5, 134.2, 135.2, 138.6, 147.4, 154.9, 155.6

[0054] After identification, the spectral data corresponded to the structural formula, and it was proved that the synthesized product was 3-benzenesulfonyl-2H-chromen-2-one with a yield of 85%.

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Abstract

The invention provides a synthesis method of a 3-benzenesulfonyl coumarin compound, and belongs to the field of organic synthesis. The 3-benzenesulfonyl coumarin compound can be directly synthesized from a coumarin compound and a sodium benzenesulfinate compound as raw materials. The synthesis method comprises the following steps: respectively adding the coumarin compound and the sodium benzenesulfinate compound into a reaction flask, and reacting for 8-10 hours at 55 DEG C-70 DEG C under the actions of iodine and dimethyl sulfoxide; after completion of the reaction, performing chromatographicseparation to obtain the 3-benzenesulfonyl coumarin compound. The synthesis method can be applied to synthesis of the 3-benzenesulfonyl coumarin compound; the synthesis method is simple, a synthesisproduct is high in yield, and the synthesis method is environment-friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 3-benzenesulfonyl coumarin compounds. Background technique [0002] Coumarin compounds widely exist in various natural products, and have various biological activities such as anti-microbial, anti-cancer, anti-HIV virus, etc., and are important intermediates for the synthesis of spices, medicines, pesticides and dyes. At present, there are many methods for synthesizing coumarin compounds. The yield was 92% (see Molecules, Vol. 16, No. 6, 2011, pp. 4379-4388); reported in 2001 the use of 2-methylbenzyl alcohol and 2-benzenesulfonyl ethyl acetate or benzenesulfonylacetonitrile, respectively Synthesized coumarins with yields of 70% and 65%, respectively (see Journal of Chemical Research-Part S, 2001, 9, pp. 394-395); in addition, in 2012, also It has been proposed to use 2-phenylthioethyl acetate to synthesize coumarins in two steps (see Indian Journal of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/12C07D311/14
Inventor 董道青王祖利丁彩真杨洪迪王艳丽
Owner QINGDAO AGRI UNIV
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