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Preparation method of poly-substituted oxazole derivative

A derivative and multi-substitution technology, which is applied in the field of preparation of multi-substituted oxazole derivatives, can solve the problems of serious pollution, use of heavy metals, poor atom economy, etc., and achieve simple synthesis method, easy purification, and scientific synthesis method reasonable effect

Active Publication Date: 2018-07-24
SHENYANG SUNSHINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above method for preparing oxazole derivatives has certain shortcomings and deficiencies: 1) need to use equivalent acid or other dehydrating agents; 2) use heavy metals, serious pollution
3) Atom economy is not good

Method used

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  • Preparation method of poly-substituted oxazole derivative
  • Preparation method of poly-substituted oxazole derivative
  • Preparation method of poly-substituted oxazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Preparation of oxazole derivative 3aa

[0024]

[0025] To a 10 ml round bottom flask was added N-phenoxyacetamide 1a (0.36 mmol, 54.4 mg), 2a (0.3 mmol, 104.4 mg) and K 2 CO 3 (0.6mmol, 82.9mg). Add 1,2-dichloroethane (2 mL), stir in a water bath at 20° C., and react for 4 hours. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), and uses a rotary evaporator to remove the solvent to obtain the target The yield of the multi-substituted oxazole derivative 3aa was 90%.

[0026] Spectrum analysis data 3aa:

[0027] 1 H NMR (500MHz, DMSO-d 6 )δ9.87(s,1H),7.49(d,J=7.5Hz,2H),7.35–7.24(m,4H),7.20(t,J=7.3Hz,1H),6.98(d,J=8.2 Hz,1H),6.88(t,J=7.5Hz,1H),2.46(s,3H); 13 C NMR(125MHz,DMSO)δ160.34,156.22,143.04,135.10,132.54,131.62,131.57,128.63,127.57,126.28,119.56,116.62,116.49,40.36,40.20,40.04,39.87,39.71,39.5...

Embodiment 2

[0029] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0030]

[0031] Spectrum analysis data 3ba:

[0032] 1 H NMR (500MHz, DMSO-d 6 )δ9.89(s, 1H), 7.47(d, J=7.5Hz, 2H), 7.30(t, J=7.7Hz, 2H), 7.23(t, J=7.4Hz, 1H), 7.15(ddt, J=12.5,9.0,4.3Hz,2H),6.95(dd,J=9.0,4.7Hz,1H),2.47(s,3H); 13 C NMR (125MHz, DMSO-d 6 )δ160.66,156.28,154.41,152.57,141.64,135.68,132.29,128.68,127.80,126.41,118.16,117.98,117.69,117.40,117.21,13.99; HRMS(ESI)m / z C calcd 16 h 13 NO 2 F+[M+H]+270.0930, found 270.0932.

Embodiment 3

[0034] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0035]

[0036] Spectrum analysis data 3ca:

[0037] 1 H NMR (500MHz, DMSO-d 6 )δ10.17(s,1H),7.45(d,J=7.4Hz,2H),7.38–7.26(m,4H),7.22(t,J=7.3Hz,1H),6.96(d,J=8.9 Hz,1H),2.46(s,3H); 13 C NMR (125MHz, DMSO-d 6 )δ160.74,155.12,141.37,135.82,132.29,131.15,130.64,128.69,127.83,126.42,122.83,118.32,118.19,40.41,40.24,40.08,39.90,39.74,39.57,39.41,13.97;HRMS(ESI)m / z calcd for C 16 h 13 NO 2 Cl + [M+H] + 286.0635, found 286.0638.

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Abstract

The invention discloses a preparation method of a novel poly-substituted oxazole derivative, and belongs to the technical field of organic synthesis. The method comprises the steps that substituted N-phenoxy amide, substituted phenylacetylene iodonium salt and potassium carbonate are added in a reaction vessel successively, a solvent 1,2-dichloroethane is added, water bath is conducted at the temperature of 20 DEG C, stirring is conducted till the 4-hour reaction is completed, a rotary evaporator is used to concentrate filter liquid to obtain a coarse product, and the target composition is obtained by separating the coarse product by means of silica gel column chromatography. The synthesis method of the poly-substituted oxazole derivative has the characteristics that the synthesis method is scientific, reasonable and simple, the yield of the target composition is higher, and the product is easy to purify and the like. The reaction equation is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted oxazole derivatives. Background technique [0002] Oxazole derivatives are a special class of five-membered heterocyclic compounds, which widely exist in natural products and medicines and have important biological activities. Such as antibacterial activity, antiproliferative activity, antifungal and viral ((a) Chem. Rev. 1975, 75, 389. (b) Chem. Res. Toxicol. 2002, 15, 269.). [0003] In addition, oxazole is also an important synthetic intermediate and an important ligand for transition metal catalysis, which provides the possibility to explore more diverse reactions (Org. Lett. 2005, 7, 2325). [0004] In view of the wide biological activity and application value of oxazole derivatives, it is of great significance to develop a new method for the practical and effective synthesis of oxazole derivatives. [0005] I...

Claims

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Application Information

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IPC IPC(8): C07D263/32
CPCC07D263/32
Inventor 文丽荣王嘉辉李卫李明
Owner SHENYANG SUNSHINE PHARMA
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