Method used for synthesizing 2, 4-oxazolidinedione compound through organic amine catalyzing CO2

A technology of oxazolidinediones and organic catalysts, applied in the direction of organic chemistry, etc., to achieve the effects of simple post-treatment process, wide range of reaction substrate types, safe and simple reaction operation

Active Publication Date: 2019-01-11
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Method used

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  • Method used for synthesizing 2, 4-oxazolidinedione compound through organic amine catalyzing CO2
  • Method used for synthesizing 2, 4-oxazolidinedione compound through organic amine catalyzing CO2
  • Method used for synthesizing 2, 4-oxazolidinedione compound through organic amine catalyzing CO2

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Under a carbon dioxide atmosphere, add a stirring bar, 0.5 mmol of N-benzyl-3-phenylpropynamide, 0.025 mmol of TBD, and 0.2 ml of tetrahydrofuran into a 10 ml Schlink bottle, and stir at 25 degrees Celsius for 1 hour, The reaction solution in the Schlinker flask was dissolved in 2 mL of dichloromethane and transferred to a 50 mL round-bottom single-necked flask. The Schlinker flask was rinsed with (3 x 2 mL) of methylene chloride, and the solvent was removed in vacuo to obtain the crude product . The crude product was separated and purified by column chromatography (eluent: dichloromethane). The yield was 98%.

[0021] The structural characterization data of the resulting product are as follows:

[0022]

[0023] 1 H NMR (400MHz, CDCl 3 )δ7.75(dd,J=7.5,2.1Hz,2H),7.49–7.40(m,5H),7.39–7.30(m,3H),6.78(s,1H),4.80(s,2H); 13 C NMR (126MHz, CDCl 3 )δ162.1,152.1,137.7,134.6,131.2,130.8,130.6,129.1,129.0,129.0,128.7,113.8,43.9; IR:1807,1740,1678,1626,1496,1451,1437,1401...

Embodiment 2

[0025] Under a carbon dioxide atmosphere, add a stir bar, 0.5 mmol of N-benzyl-3-(4-fluorophenyl) propynamide, 0.025 mmol of TBD, and 0.2 mL of tetrahydrofuran to a 10 mL Schlinker flask at 25 °C After stirring for 1 hour, the reaction solution in the Schlinker flask was dissolved in 2 mL of dichloromethane and transferred to a 50 mL round-bottomed single-necked flask. The crude product was obtained after solvent. The crude product was separated and purified by column chromatography (eluent: dichloromethane). The yield was 99%.

[0026] The structural characterization data of the resulting product are as follows:

[0027]

[0028] 1 H NMR (400MHz, CDCl 3 )δ7.73(dd, J=8.1,5.7Hz,2H),7.44(d,J=7.4Hz,2H),7.40–7.27(m,3H),7.10(t,J=8.4Hz,2H), 6.72(s,1H),4.78(s,2H). 13 C NMR (101MHz, CDCl 3 )δ165.0, 162.2(d, J=54.1Hz), 151.9, 137.2(d, J=2.7Hz), 134.4, 133.2(d, J=8.6Hz), 129.0, 129.0, 128.6, 127.0(d, J=3.4 Hz), 116.3(d, J=21.9Hz), 112.5, 43.9. IR: 1809, 1736, 1671, 1439, 1407...

Embodiment 3

[0030] Under a carbon dioxide atmosphere, add a stirring bar, 0.5 mmol of N-benzyl-3-(p-tolyl) propynamide, 0.025 mmol of TBD, and 0.2 ml of tetrahydrofuran to a 10 ml Schlink flask, and stir at 25 degrees Celsius for 1 After 2 hours, the reaction solution in the Schlinker flask was dissolved in 2 ml of dichloromethane and transferred to a 50-ml round-bottom single-necked flask. The Schlinker flask was rinsed with (3 × 2 ml) of dichloromethane, and the solvent was removed in vacuo. A crude product is obtained. The crude product was separated and purified by column chromatography (eluent: dichloromethane). The yield was 83%.

[0031] The structural characterization data of the resulting product are as follows:

[0032]

[0033] 1 H NMR (500MHz, CDCl 3 )δ7.62(d, J=8.1Hz, 2H), 7.44(d, J=6.7Hz, 2H), 7.39–7.28(m, 3H), 7.21(d, J=8.0Hz, 2H), 6.74( s,1H),4.77(s,2H),2.37(s,3H). 13 C NMR (126MHz, CDCl 3)δ162.2, 152.2, 141.3, 137.1, 134.6, 131.3, 129.9, 129.0, 129.0, 128.6, 128...

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Abstract

The invention provides a method used for synthesizing 2, 4-oxazolidinedione compound through organic amine catalyzing CO2, and belongs to the technical field of organic synthesis, pesticide, and medical chemistry. The method comprises following steps: acetylene amide raw material and a solvent are introduced into a reaction bottle containing a magneton, an organic base is added as a catalyst, thereaction bottle is introduced into a Schlink bottle filled with carbon dioxide gas, stirring reaction is carried out for 1 to 6h at room temperature, after reaction, an obtained reaction liquid is pumped out from the reaction bottle, an obtained crude product is subjected to column chromatography so as to obtain the 2, 4-oxazolidinedione compound. According to the method, the simple organic base of a catalytic amount is adopted to replace a conventional metal catalyst; reaction is clean; reaction conditions are mild; function group tolerance is high; conversion rate and stereoselectivity are high, and the application prospect in the fields of organic synthesis, pesticide, and medicine is promising.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, pesticide and pharmaceutical chemical synthesis, and relates to the synthesis of 2,4-oxazolidinedione by efficiently catalyzing the carboxycyclization reaction of carbon dioxide and alkyne amide derivatives with cheap and easy-to-obtain commercial organic amines as organic catalysts method of compounds. Background technique [0002] 2,4-Oxazolidinedione heterocyclic compounds, as a class of biologically active substances and important structural units of related drugs, play an important role in the fields of medicine and pesticides, and can be used as antiepileptic drugs, fungicides, and anti-inflammatory drugs , herbicides, etc. In recent years, because carbon dioxide is a kind of abundant and easy-to-obtain C1 resource, the construction of heterocyclic compounds with various structures by using its participation in cyclization reactions has attracted the attention of many researchers...

Claims

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Application Information

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IPC IPC(8): C07D263/44C07D409/06
CPCC07D263/44C07D409/06
Inventor 周辉穆森张瑞张慧
Owner DALIAN UNIV OF TECH
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