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Preparation method of oxazole derivative

A technology of derivatives and oxazoles, applied in the field of preparation of oxazole derivatives, can solve the problems of poor atom economy and harsh reaction conditions, and achieve the effects of scientific and reasonable synthesis method, easy purification and high atom economy

Active Publication Date: 2018-12-21
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Utilize above-mentioned method to prepare oxazole derivative in laboratory, have obvious shortcoming: 1) need to use equivalent acid or other dehydrating agent; 2) harsh reaction condition; 3) atom economy is not good

Method used

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  • Preparation method of oxazole derivative
  • Preparation method of oxazole derivative
  • Preparation method of oxazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the preparation of oxazole derivative 3a

[0023]

[0024] Add p-methylenebenzoquinone 1a (0.5mmol, 162.2mg), N-propargylbenzamide 2a (0.75mmol, 119.4mg) and InCl to a 25mL single-necked flask 3 (0.05 mmol, 11.1 mg). Add 1,2-dichloroethane (2.5 mL), stir in an oil bath at 70° C., and react for 3 hours. After the reaction is complete, cool to room temperature, remove the solvent with a rotary evaporator, and separate the residue through column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=20 / 1), and the solid obtained by rotary evaporation is washed with n-hexane Washing twice gave the oxazole derivative 3a as a white solid with a yield of 94%.

[0025] Spectral analysis data 3a:

[0026] 1 H NMR (CDCl 3 ,500MHz)δ7.95–7.89(m,2H),7.48–7.37(m,3H),7.03(dd,J=8.6,8.7Hz,4H),7.05(s,2H),6.63(s,1H) ,5.08(s,1H,missing after deuteriation),4.28(t,J=8.0Hz,1H),3.79(s,3H),3.41(d,J=8.0Hz,2H),1.41(s,18H); 13 C NMR (CDCl 3 ,125MHz)δ160.39...

Embodiment 2

[0028] Replace 2a in Example 1 with 2b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0029]

[0030] Spectrum analysis data 3b:

[0031] 1 H NMR (CDCl 3 ,500MHz)δ7.65(dd,J=8.5,8.6Hz,4H),7.00(dd,J=8.6,8.7Hz,4H),7.01(s,2H),6.61(s,1H),5.06(s ,1H),4.24(t,J=8.0Hz,1H),3.77(s,3H),3.38(d,J=7.9Hz,2H),1.38(s,18H); 13 C NMR (CDCl 3 ,125MHz)δ159.52,158.08,152.21,151.77,135.95,135.76,134.24,131.83,128.62,127.38,126.64,125.11,124.13,124.03,113.82,77.20,76.94,76.69,55.17,49.12,34.30,32.92,30.28,30.26 ,30.23; HRMS(ESI)m / zcalcd for C 32 h 37 NO 3 Br + [M+H] + 562.1957, found 562.1956.

Embodiment 3

[0033] Replace 2a in Example 1 with 2c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0034]

[0035] Spectrum analysis data 3c:

[0036] 1 H NMR (CDCl 3 ,500MHz)δ7.51(dd,J=8.1,7.9Hz,4H),7.01(dd,J=8.5,8.5Hz,4H),7.03(s,2H),6.59(s,1H),5.07(s ,1H),4.26(t,J=7.9Hz,1H),3.77(s,3H),3.38(d,J=7.9Hz,2H),2.39(s,3H),1.39(s,18H); 13 C NMR (CDCl 3 ,125MHz)δ160.61,157.99,152.18,151.00,139.97,136.07,135.65,134.36,129.30,128.66,125.87,125.05,124.75,124.07,113.77,77.23,76.97,76.72,55.17,49.06,34.31,32.94,30.25,21.43 ;HRMS(ESI)m / zcalcd for C 33 h 40 NO 3 + [M+H] + 498.3008,found 498.3001.

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Abstract

The invention discloses a preparation method of an oxazole derivative, belonging to the technical field of organic synthesis. The method comprises the following steps: adding substituted p-methylene benzoquinone, substituted N-propargylamide and indium trichloride in a reactor, adding a solvent 1,2-dichloroethane, heating until completing reaction, concentrating filtrate by using a rotary evaporator to obtain a crude product, and isolating through column chromatography to obtain a product. The synthetic method of the oxazole derivative provided by the invention is scientific and reasonable, and is characterized in that the synthetic method is simple, the atom economy is high and the product is easy to purify. 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 oxazole derivatives. Background technique [0002] Among various synthetic and naturally occurring heterocyclic structures, the oxazole nucleus is one of the most important simple heterocyclic rings. [0003] Oxazole derivatives widely exist in various natural products and drugs, and have significant biological activities. Such as antifungal, antiviral, antibacterial and antiproliferative activities ((a) Chemistry of Heterocyclic Compounds, Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, 2003; Part B, 2004. (b) Curr.Top.Med.Chem. 2016, 16, 3582. (c) Bioorganic Med. Chem. Lett. 2005, 15, 5284). In addition, oxazole is also a useful synthetic intermediate in organic synthesis and an important ligand for transition metal catalysis (Org. Lett. 2005, 7, 2325). [0004] In view of the wide application of oxazole derivatives, it ...

Claims

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Application Information

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IPC IPC(8): C07D263/32C07D413/04C07D413/06
CPCC07D263/32C07D413/04C07D413/06
Inventor 文丽荣王加琦李卫李明
Owner QINGDAO UNIV OF SCI & TECH
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