Visible light promoted synthesis method of seleno oxazolidine-2. 4-diketone

A technology of selenooxazolidine and its synthesis method, which is applied in the direction of organic chemistry, can solve problems that have not been reported, and achieve the effects of good application potential, good compatibility, and simple operation

Active Publication Date: 2021-11-05
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the literature survey shows that the method of synthesizing selenooxazolidine-2,4-dione based on the participation of visible light has not been reported so far.

Method used

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  • Visible light promoted synthesis method of seleno oxazolidine-2. 4-diketone
  • Visible light promoted synthesis method of seleno oxazolidine-2. 4-diketone
  • Visible light promoted synthesis method of seleno oxazolidine-2. 4-diketone

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preparation example Construction

[0021] The present invention provides the following technical scheme: a visible light-promoted synthetic method of selenooxazolidine-2.4-dione, the steps are as follows: in an organic solvent, with N-Boc-protected propylene having the structure shown in formula (I) Amide, the diselenide of the structure shown in formula (II) is the reaction raw material, reacts under the irradiation of visible light, after the reaction is finished, the reaction solution is decompressed to remove the solvent to obtain the crude product, and the crude product is purified by column chromatography to obtain the formula (III ) a selenooxazolidine-2.4-dione compound of the structure shown in );

[0022] The reaction equation is shown in the following formula:

[0023]

[0024] wherein R in the compound of formula (I) 1 and R 2 is an H atom, an alkyl group and an aryl group, and the compound of formula (II) adopts diaryl diselenide and dialkyl diselenide.

Embodiment 1

[0026] The reaction equation is shown in the following formula:

[0027]

[0028] At room temperature, N-Boc-N-(4-chlorophenyl)-2-methacrylamide (0.25 mmol), diphenyl diselenide, (0.25 millimoles), acetonitrile (2 milliliters), after adding, place a 23-watt white compact fluorescent lamp at a distance of 3 centimeters from the reaction tube, and react at room temperature for 36 hours. After the reaction was completed, the organic phase was removed by a rotary evaporator. The solvent and the residue were purified with a silica gel column (silica gel specification: 200-300 mesh, eluent petroleum ether / ethyl acetate=20:1) to obtain 93 mg of white solid with a yield of 94%.

[0029] The obtained product nuclear magnetic spectrum data are: 11 H NMR (400MHz, CDCl 3 ): δ7.56-7.52(m, 2H), 7.46(d, J=8.8Hz, 2H), 7.39(d, J=8.8Hz, 2H), 7.30-7.25(m, 3H), 3.46(d, J=13.9 Hz, 1H), 3.41(d, J=13.9Hz, 1H), 1.77(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ173.2, 152.8, 134.8, 133.6, 129.5, 129.4...

Embodiment 2

[0031] The reaction equation is shown in the following formula:

[0032]

[0033] At room temperature, N-Boc-N-(4-bromophenyl)-2-methacrylamide (0.25 mmol), diphenyl diselenide, (0.25 millimoles), acetonitrile (2 milliliters), after adding, place a 23-watt white compact fluorescent lamp at a distance of 3 centimeters from the reaction tube, and react at room temperature for 36 hours. After the reaction was completed, the organic phase was removed by a rotary evaporator. The solvent and the residue were purified with a silica gel column (silica gel specifications: 200-300 mesh, eluent petroleum ether / ethyl acetate = 25:1) to obtain 104 mg of a white solid with a yield of 95%.

[0034] The obtained product nuclear magnetic spectrum data are: 1 H NMR (400MHz, CDCl 3 ):δ7.54(d,J=8.8Hz,2H),7.49–7.42(m,2H),7.25(d,J=8.8Hz,2H),7.23–7.16(m,3H),3.38(d, J=13.9Hz, 1H), 3.33(d, J=13.9Hz, 1H), 1.69(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ172.1, 151.7, 132.5, 131.5, 128.9, 128.4, 127.6,...

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Abstract

The invention discloses a visible light promoted synthesis method of seleno-oxazolidine-2, 4-diketone, the method comprises the following steps: taking N-Boc protected acrylamide and diselenide as reaction raw materials, stirring and reacting at a certain temperature under the irradiation of a light source to obtain a seleno-oxazolidine-2, 4-diketone compound. According to the method, the reaction conditions are simple, the yield of the product is high, and the preparation from the acrylamide raw material to the seleno-oxazolidine-2, 4-diketone heterocyclic compound is realized for the first time; the method also has the advantages of being insensitive to air, wide in substrate range and the like, develops a new synthesis route and method for the seleno-oxazolidine-2, 4-diketone heterocyclic compound, and has good application potential and research value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis chemistry, in particular to a visible light-promoted synthesis method of selenooxazolidine-2.4-dione. Background technique [0002] Oxazolidine-2,4-dione compounds are important intermediates in organic synthesis and important structural units in biologically active molecules. Such compounds have wide applications in the fields of medicine and agriculture, such as having anti-diabetic, anti-epileptic, anti-inflammatory activities, and being used as fungicides and herbicides. Therefore, the development of efficient methods for the synthesis of oxazolidine-2,4-dione compounds has been widely concerned by organic chemists and medicinal chemists. Commonly used synthetic methods include condensation of α-hydroxyamide and carbonate or reaction of α-hydroxyester with urea or isocyanate ((a) J.W.Clark-Lewis, Chem.Rev.1958,58,63-99; (b) R. Maity, S. Naskar, K. Mal, S. Biswas, I. Das, Adv. Synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/44C07D413/06
CPCC07D263/44C07D413/06
Inventor 刘功清周晨凡张云倩凌勇
Owner NANTONG UNIVERSITY
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