Preparation method of N-substituted oxazolone polymer derivatives

A technology for oxazolones and derivatives, applied in the field of N-substituted oxazolones polymeric derivatives and preparation, can solve problems such as long reaction time, and achieve the effect of mild and efficient reaction conditions

Inactive Publication Date: 2015-07-22
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After literature search, it is found that there are only two examples of this type of dimerization or ring-forming reaction reported in the literature, such as the method used by G.Cum et al. (Tetrahedron Vol.36.pp.745to 751) is based on 50%-65 % of sulfuric acid as a reagent, but it requires a long reaction time during cyclization

Method used

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  • Preparation method of N-substituted oxazolone polymer derivatives
  • Preparation method of N-substituted oxazolone polymer derivatives
  • Preparation method of N-substituted oxazolone polymer derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: 3-allyl-5-(3-allyl-2-oxooxazolidin-4-yl)oxazol-2(3H)-one

[0037]

[0038] In the DCM solution (2ml) of reaction substrate 1a (77.6mg, 0.62mmol), add BF dropwise 3 ·Et 2 O (41 μL, 0.5 equiv.), seal the tube. The reaction mixture was stirred at 50°C for 12 hours, and after the completion of the reaction was monitored with a TLC plate, it was washed with saturated NaHCO 3 (5ml) to quench the reaction and stir for 5 minutes. DCM was extracted 3 times (5mL x 3), the organic phases were combined and washed with water (10mL), saturated NaCl (10mL), and finally with NaCl 2 SO 4 After drying, filtration and rotary evaporation, the crude product was obtained. The crude product was subjected to silica gel column chromatography to obtain pure product 2a (yield 98%).

[0039] Colorless oily liquid; Rf=0.21 (Hexane / EtOAc=3 / 2); 1 H NMR (CDCl 3 ,400MHz):δ6.51(1H,s),5.88-5.82(1H,m),5.76-5.70(1H,m),5.34-5.15(4H,m),4.61(1H,dd,J=9.2, 7.2Hz), 4.60(1H,t,J=8.8Hz), 4.31...

Embodiment 2

[0040] Example 2: 5-(2-oxo-3-propyloxazolidin-4-yl)-3-propyloxazol-2(3H)-one

[0041]

[0042] In DCM solution (2ml) of reaction substrate 1b (79mg, 0.62mmol), add BF dropwise 3 ·Et 2 O (41 μL, 0.5 equiv.), seal the tube. The reaction mixture was stirred at 50°C for 12 hours, and after the completion of the reaction was monitored with a TLC plate, it was washed with saturated NaHCO 3 (5ml) to quench the reaction and stir for 5 minutes. DCM was extracted 3 times (5mL x 3), the organic phases were combined and washed with water (10mL), saturated NaCl (10mL), and finally with NaCl 2 SO 4 After drying, filtration and rotary evaporation, the crude product was obtained. The crude product was subjected to silica gel column chromatography to obtain pure product 2b (yield 85%).

[0043] Colorless oily liquid; Rf=0.22 (Hexane / EtOAc=3 / 2); 1 H NMR (CDCl 3 ,600MHz): δ6.54(1H,s),4.61(1H,dd,J=8.4,6.6Hz),4.45(1H,t,J=9.3Hz),4.30(1H,dd,J=8.4,6.6 Hz),3.55-3.52(2H,m),3.39-3.34(1H,m),3...

Embodiment 3

[0044] Example 3: 3-Benzyl-5-(3-benzyl-2-oxooxazolidin-4-yl)oxazol-2(3H)-one

[0045]

[0046] In the DCM solution (2ml) of reaction substrate 1c (109mg, 0.62mmol), add BF dropwise 3 ·Et 2 O (41 μL, 0.5 equiv.), seal the tube. The reaction mixture was stirred at 50°C for 12 hours, and after the completion of the reaction was monitored with a TLC plate, it was washed with saturated NaHCO 3 (5ml) to quench the reaction and stir for 5 minutes. DCM was extracted 3 times (5mL x 3), the organic phases were combined and washed with water (10mL), saturated NaCl (10mL), and finally with NaCl 2 SO 4 After drying, filtration and rotary evaporation, the crude product was obtained. The crude product was subjected to silica gel column chromatography to obtain pure product 2c (yield 87%).

[0047] White solid (melting point: 125-126 °C); Rf = 0.33 (Hexane / EtOAc = 3 / 2); 1 H NMR (CDCl3, 400MHz): δ7.40-7.14 (10H, m), 6.23 (1H, s), 4.69 (1H, d, J=15.6Hz), 4.66 (2H, s), 4.38-4.29 (3H ,...

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Abstract

The invention relates to a preparation method of N-substituted oxazolone polymer derivatives. An available reagent boron trifluoride diethyl ether is taken as a catalyst and influences dimerization and cascading dimerization / cyclization among N-substituted oxazolone molecules under the mild reaction condition. The method is insensitive to water in a reaction system, the same reaction can be performed under the condition of water, and the same productive rate and speed are kept. The novel reaction condition and the efficient transformation mode can be more applied to synthesis of various molecules and industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and relates to N-substituted oxazolone polymer derivatives and a preparation method. Background technique [0002] In the fields of organic synthesis and medicinal chemistry, efficient and environmentally friendly synthesis of complex and diverse molecular structures has always been the goal of laboratories and industries. This goal is difficult and challenging in practice. [0003] According to Argade et al. (E-Journal of Chemistry Vol.5, No.1, pp.120-129, January 2008), oxazolone has become one of the most attractive molecules among heterocyclic compounds due to its wide range of biological activities First, it is also an important intermediate in the field of total synthesis of natural products. However, the research on the organic reaction and chemical activity of 2,3-hydro-1,3-oxazolone has been lagging behind, and its application in the synthesis of natura...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/38C07D498/14
CPCY02P20/55C07D263/38C07D498/14
Inventor 邹成周兴华曹蓓徐化成P·K·阿加瓦尔C·K·I·那迦贺耘
Owner CHONGQING UNIV
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