Synthesis method of dihydrooxazole compound

A technology of dihydrooxazole and synthetic methods, which is applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve the problems of cumbersome reaction steps, low reaction efficiency, long reaction time, etc. To achieve the effect of shortening the reaction time, speeding up the reaction rate and green reaction conditions

Pending Publication Date: 2022-05-24
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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Problems solved by technology

[0004] Purpose of the invention: the present invention aims at the deficiencies of the prior art, and provides a method for synthesizing dihydrooxazole derivatives by means of a microchannel reaction device, so as to solve the existing problems of the prior art such as cumbersome reaction steps, long reaction time, and low reaction efficiency. The problem is to realize the synthesis of dihydrooxazole derivatives simply and efficiently without using metal catalysts

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  • Synthesis method of dihydrooxazole compound
  • Synthesis method of dihydrooxazole compound
  • Synthesis method of dihydrooxazole compound

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Embodiment 1

[0039] 1 mmol (0.261 g) of (2E,4E)-4-(acetoxyimino)-4-phenylbut-2-enoic acid ethyl ester, 4 mmol of ethyl trifluoropyruvate (0.680 g), dichloro Dicyanobenzoquinone (0.3405g) was dissolved in 20ml of toluene, and the flow rate was 0.2mL / min into the microchannel reactor (the inner diameter of the copper tube of the microreactor was 1mm and the volume of the copper tube was 4mL) and reacted at 120°C for 8min. The organic phase was obtained from the discharge of the microreactor, and the crude product was obtained by vacuum concentration, and separated by column chromatography with a developing solvent with a ratio of petroleum ether to ethyl acetate of 5:1, and the target product was obtained as shown in Table 1, and the yield was 87%. . 1H NMR (400MHz, Chloroform-d) δ 7.75 (d, J=7.4Hz, 2H), 7.51–7.47 (m, 1H), 7.41 (t, J=7.3Hz, 2H), 5.96 (dd, J= 7.6, 3.8Hz, 1H), 4.27 (q, J=7.0Hz, 2H), 4.10 (q, J=7.0Hz, 2H), 2.89–2.78 (m, 2H), 1.28 (t, J=7.0Hz, 3H),1.19–1.15(m,3H)ppm; 13 C NMR...

Embodiment 2

[0041] 1 mmol (0.275 g) of (2E,4E)-4-(acetoxyimino)-4-(p-tolyl)but-2-enoic acid ethyl ester, 4 mmol of ethyl trifluoropyruvate (0.680 g) , Dichlorodicyanobenzoquinone (0.3405g) was dissolved in 20ml of toluene, and the flow rate was 0.2mL / min into the microchannel reactor (the inner diameter of the copper tube of the microreactor was 1mm, and the volume of the copper tube was 4mL) at 120 ° C. The reaction was carried out for 8 minutes. The microreactor is discharged to obtain an organic phase, which is concentrated in vacuo to obtain a crude product, which is separated by a developing solvent column chromatography with a petroleum ether and ethyl acetate ratio of 5:1, and the target product can be obtained. See Table 1, and the yield is 83%. . 1 H NMR (400MHz, Chloroform-d) δ 7.72 (d, J=8.2Hz, 2H), 7.29 (d, J=8.1Hz, 2H), 6.02 (dd, J=7.6, 3.7Hz, 1H), 4.35 (q, J=7.1Hz, 2H), 4.18 (q, J=7.2Hz, 2H), 1.25 (t, J=7.1Hz, 3H), 2.96–2.85 (m, 2H), 2.42 (s, 3H) ,1.36(t,J=7.1Hz,3H)ppm; ...

Embodiment 3

[0043] 1 mmol (0.295 g) of (2E,4E)-4-(acetoxyimino)-4-(p-chlorophenyl)but-2-enoic acid ethyl ester, 4 mmol of ethyl trifluoropyruvate (0.680 g) ), dichlorodicyanobenzoquinone (0.3405g) was dissolved in 20ml of toluene, and the flow rate was 0.2 mL / min into the microchannel reactor (the inner diameter of the microreactor copper tube was 1mm, and the volume of the copper tube was 4mL) at 120°C The reaction was continued for 8 min. The microreactor is discharged to obtain an organic phase, which is concentrated in vacuo to obtain a crude product, which is separated by a developing solvent column chromatography with a petroleum ether and ethyl acetate ratio of 5:1, and the target product can be obtained. See Table 1, and the yield is 85%. . 1 H NMR (400 MHz, Chloroform-d) δ 7.78 (d, J=8.6Hz, 2H), 7.47 (d, J=8.6Hz, 2H), 6.00 (dd, J=6.4, 4.6Hz, 1H), 4.36(q,J=7.1Hz,2H),4.17(q,J=7.1Hz,2H),2.94–2.85(m,2H),1.36(t,J=7.1Hz,3H),1.25(t,J =7.1Hz, 3H)ppm; 13 C NMR (100MHz, Chloroform-d) δ...

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Abstract

The invention discloses a synthesis method of a dihydrooxazole compound shown as III, which comprises the following steps: taking an alpha, beta-unsaturated ketoxime ester compound I and ethyl trifluoropyruvate II as reaction raw materials, adding dichloro dicyanobenzoquinone, and continuously reacting by using a microchannel reaction device to prepare the dihydrooxazole compound. Compared with the prior art, the method has the advantages that the alpha, beta-unsaturated ketoxime ester compound and the ethyl trifluoropyruvate are used as substrates to prepare the novel dihydrooxazole compound, multi-component reaction is avoided, and the product is rapidly and efficiently synthesized. In the formula (I), R1 is selected from non-substituted or substituted phenyl, halogen, C1-C5 alkyl, C1-C5 alkoxy, furyl, naphthyl or C1-C5 alkyl; r2 is selected from C1-C5 ester groups; the substituted phenyl group is selected from phenyl groups substituted by halogen, C1-C5 alkyl groups or C1-C5 alkoxy groups.

Description

technical field [0001] The invention belongs to the technical field of preparation of dihydrooxazole compounds, in particular to a method for synthesizing dihydrooxazole compounds by utilizing a microchannel reaction device. Background technique [0002] Dihydrooxazoles are considered to be an important class of moieties often found in many natural products and medicines with different biological activities. Examples include antitumor, antibacterial, antifungal, antimalarial and antiproliferative properties, and as an inhibitor of GlcNAc-Ins deacetylase. In addition, they also play key roles in asymmetric transformations as chiral ligands. Therefore, we put great effort into developing effective methods for these scaffolds. Despite considerable progress, the development of versatile and efficient methods for the direct construction of dihydrooxazoles with various functional groups is still urgent and highly desirable. [0003] At present, the preparation methods of dihydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/16C07D413/04B01J19/00
CPCC07D263/16C07D413/04B01J19/0093
Inventor 沈磊延欢段金电徐高晨张赛邬庆欢季栋李玉光郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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