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Synthetic method of chromanone compounds

A synthetic method and compound technology, which is applied in the field of synthesis of chromanone compounds, can solve the problems of not being chromanone compounds, uneconomical, and unfriendly to the environment, and achieve simple reaction system, effective recycling, and short reaction time Effect

Active Publication Date: 2020-11-17
吉林警察学院 +1
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Problems solved by technology

However, in the above preparation process, the metal silver catalyst used is expensive and used in a large amount, and the organic solvent is not only not recyclable, but also unfriendly to the environment.
Therefore, the method currently provided is not economical, nor is it the optimal solution in the experimental synthesis of chromanones

Method used

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  • Synthetic method of chromanone compounds
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  • Synthetic method of chromanone compounds

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preparation example Construction

[0023] The embodiment of the present invention provides a synthetic method of chromanone compounds, comprising the following steps:

[0024] S1: Add 2-(allyloxy)benzaldehyde compounds and sodium benzenesulfinate compounds to the reactor respectively, under the action of a catalyst and a deep eutectic solvent, react in an airtight condition at 60-100°C 5-8 hours.

[0025] In this step, 2-(allyloxy)benzaldehyde compounds and sodium benzenesulfinate compounds are used to synthesize chromanone compounds, specifically, under heating conditions, ferric chloride and persulfate Under the action of the deep eutectic solvent, the hydrogen atom of the sodium benzene sulfinate compound is captured to generate a sulfinic acid free radical, and the sulfinic acid free radical passes through the double bond in the 2-(allyloxy)benzaldehyde compound Addition generates carbon free radicals, which then undergo intramolecular cyclization reactions with aldehyde groups to generate oxygen free radi...

Embodiment 1

[0044] Add 1mmol to the reactor 1mmol sodium benzenesulfinate, 2mmol potassium persulfate, 0.05mmol FeCl 3 ·6H 2 O and 2ml of deep eutectic solvent, under air condition of 80 ℃ airtight heat reaction 6 hours;

[0045]

[0046] Carry out nuclear magnetic spectrum analysis to above-mentioned white solid powder, data is as follows:

[0047] 1 H NMR (500MHz, CDCl 3 )δ8.03-7.95(m,2H),7.83(dd,J=7.9,1.6Hz,1H),7.69(t,J=7.5Hz,1H),7.61(t,J=7.7Hz,2H), 7.54-7.47(m,1H),7.01(dd,J=15.7,7.8Hz,2H),5.01(dd,J=11.4,5.3Hz,1H),4.35(t,J=11.8Hz,1H),3.99 (dd, J=14.6, 2.3Hz, 1H), 3.51-3.36(m, 1H), 3.01(dd, J=14.6, 10.1Hz, 1H);

[0048] 13 C NMR (126MHz, CDCl 3 )δ189.9, 161.7, 138.9, 136.60, 134.2, 129.6, 128.0, 127.6, 121.8, 119.9, 118.0, 69.62, 51.75, 40.8;

[0049] After identification, the spectral data corresponds to the structural formula, proving that the synthesized product is 3-((benzenesulfonyl)methyl)benzopyran-4-one with a yield of 90%.

Embodiment 2

[0051] Add 1mmol to the reactor 1mmol sodium p-chlorobenzenesulfinate, 2mmol potassium persulfate, 0.05mmol FeCl 3 ·6H 2 O and 2ml of deep eutectic solvent, under air condition of 60 ℃ of airtight heating reaction for 8 hours; After the reaction is finished, carry out column chromatography separation, obtain following P2 compound:

[0052]

[0053] Carry out nuclear magnetic spectrum analysis to above-mentioned white solid powder, data is as follows:

[0054] 1 H NMR (500MHz, CDCl 3 )δ7.91(d, J=7.7Hz, 2H), 7.83(d, J=7.9Hz, 1H), 7.58(d, J=7.6Hz, 2H), 7.51(t, J=7.8Hz, 1H) ,7.02(dd,J=18.6,7.9Hz,2H),5.00(dd,J=11.4,5.2Hz,1H),4.35(t,J=11.8Hz,1H),3.97(d,J=14.6Hz, 1H), 3.50-3.32(m, 1H), 3.01(dd, J=14.3, 10.2Hz, 1H);

[0055] 13 C NMR (126MHz, CDCl 3 )δ189.8, 161.7, 141.1, 137.3, 136.7, 129.9, 129.5, 127.6, 121.8, 119.9, 118.1, 69.6, 51.8, 40.8;

[0056] After identification, the spectrum data corresponds to the structural formula, proving that the synthesized product is 3...

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Abstract

The invention provides a synthesis method of chromanone compounds, belongs to the field of organic synthesis, and aims at solving the technical problems that in the prior art, expensive metal silver catalysts are mostly used and are large in dosage when chromanone compounds are synthesized, and adopted organic solvents are not environmentally friendly. According to a technical scheme, the method comprises the following steps: respectively adding a 2-(allyloxy) benzaldehyde compound and a sodium benzenesulfinate compound into a reactor, and carrying out a closed reaction for 6-8 hours under theair condition at 60-100 DEG C under the action of a catalyst and a eutectic solvent; and after the reaction is finished, carrying out column chromatography separation to obtain the chromanone compound. The synthesis method provided by the invention is simple in reaction system, and does not need to use an expensive metal catalyst, the solvent can be recycled, so that a brand-new method is provided for green synthesis of chromanone compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing chromanone compounds. Background technique [0002] Chromanone compounds have a variety of biological activities, and have achieved satisfactory multi-faceted effects in recent years, and have attracted more and more attention from chemical researchers all over the world. At present, the preparation method of existing available chromanone compounds is to utilize 2-(allyloxy)benzaldehyde compounds and acid compounds to react at high temperature under the conditions of expensive metal silver catalyst and organic solvent Prepared (Chem.Commun.2016,52,3661 and Adv.Synth.Catal.2017,359,2390-2395 are described). However, in the above-mentioned preparation process, the metal silver catalyst used is expensive and used in a large amount, and the organic solvent is not only not recyclable, but also unfriendly to the environment. Therefore, the method currently p...

Claims

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Application Information

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IPC IPC(8): C07D311/22
CPCC07D311/22Y02P20/584
Inventor 赵苏艳陈德茂韩晴晴孙媛媛王艳丽杨洪迪丁彩真杨少慧宋敬城李娜王祖利
Owner 吉林警察学院
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