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A kind of preparation method of 2,3,6-trisubstituted pyrazine nitrogen oxygen compound

A compound and three-substitution technology, applied in the field of preparation of 2,3,6-trisubstituted pyrazine nitrogen-oxygen compounds, can solve environmental pollution and other problems

Active Publication Date: 2020-09-04
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] To sum up, although there are many synthetic methods of pyrazine derivatives, there are few reports on the synthetic methods without metal and acid-base participation. Most of the existing methods need to be carried out under acid-base conditions, resulting in certain environmental pollution

Method used

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  • A kind of preparation method of 2,3,6-trisubstituted pyrazine nitrogen oxygen compound
  • A kind of preparation method of 2,3,6-trisubstituted pyrazine nitrogen oxygen compound
  • A kind of preparation method of 2,3,6-trisubstituted pyrazine nitrogen oxygen compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: The preparation method of 2-ethoxycarbonyl-6-(4-fluorobenzoyl)-3-phenylpyrazine nitrogen oxide

[0032] In a 10 mL dry reaction tube, the starting material Z-3-phenyl-3-(3-(4-fluorophenyl)propynylamino)ethyl acrylate (0.162g, 0.5mmol) and t- Butyl nitrite (0.103g, 1mmol), 10mL dichloroethane, and the mixed system were reacted at room temperature 25°C for 30min. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure. The target product (119 mg, yield 71%) was obtained by column chromatography.

[0033] Melting point: 135-137°C. Data representation: 1 H NMR (400MHz, CDCl 3 ):8.74(s,1H),7.96–7.88(m,2H), 7.79(dd,J=8.1,1.5Hz,2H),7.59–7.49(m,3H),7.20(dd,J=11.9,5.3 Hz,2H),4.37(q,J=7.1Hz,2H),1.24(t,J=7.1Hz,3H)....

Embodiment 2

[0034] Embodiment 2: the preparation method of 2-ethoxycarbonyl-6-benzoyl-3-phenylpyrazine nitrogen oxide

[0035] In a 10 mL dry reaction tube, under an oxygen atmosphere, the starting materials Z-3-phenyl-3-(3-phenylpropynylamino) ethyl acrylate (0.153 g, 0.5 mmol) and tert-butyl nitrite ( 0.103g, 1mmol), 10mL dichloroethane, and the mixed system was reacted at room temperature 25°C for 30min. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure. The target product (105 mg, yield 66%) was obtained by column chromatography.

[0036] Melting point: 103-105°C. Data representation: 1 H NMR (400MHz, CDCl 3 ):8.72(s,1H),7.87-7.89(m,2H), 7.76-7.78(m,2H),7.64-7.67(m,1H),7.50-7.55(m,5H),4.35(q,J =8.0Hz, 2H), 1.23(t, J = 8.0Hz...

Embodiment 3

[0037] Embodiment 3: the preparation method of 2-ethoxycarbonyl-6-(4-methylbenzoyl)-3-phenylpyrazine nitrogen oxide

[0038] In a 10mL dry reaction tube, under an oxygen atmosphere, the raw materials Z-3-phenyl-3-(3-(4-methylphenyl)propynylamino)ethyl acrylate (0.160g, 0.5mmol) and Tert-butyl nitrite (0.103g, 1mmol), 10mL of dichloroethane, and the mixed system was reacted at room temperature 25°C for 30min. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure. The target product (103 mg, yield 62%) was obtained by column chromatography.

[0039] Melting point: 85-87°C. Data representation: 1 H NMR (400MHz, CDCl 3 ):8.71(s,1H),7.78(t,J=9.4Hz,4H), 7.57–7.49(m,3H),7.33(d,J=8.0Hz,2H),4.37(q,J=7.1Hz ,2H),2.47(s,3H),1.25(t,...

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Abstract

The invention discloses a high-efficiency preparation method of 2,3,6-trisubstituted pyrazine N-oxide compounds, and belongs to the technical field of fine chemicals. The method comprises the step ofperforming a reaction by using a compound represented by a formula (I) shown in the description as a substrate and a specific nitrite as an oxidant at a reaction temperature of room temperature 25 DEGC for 30 min in an oxygen atmosphere to synthesize the target product. The synthetic method provided by the invention is simple, and has mild reaction conditions, a better yield, and good applicationprospects.

Description

technical field [0001] The invention relates to a preparation method of 2,3,6-trisubstituted pyrazine nitrogen-oxygen compounds, belonging to the technical field of fine chemicals. Background technique [0002] As a very important class of six-membered nitrogen-containing heterocyclic compounds, pyrazines widely exist in the molecular skeletons of natural products and bioactive drugs; they are important intermediates in the production of medicines, pesticides, new polymer materials, spices and dyes. In recent decades, pyrazine derivatives have been widely studied in the field of pesticide and pharmaceutical research and development, and have been highly valued. Therefore, the synthesis of pyrazine compounds and their application in new drugs and pesticides have become a hot spot of scientific research. [0003] There have been many reports on the synthesis of pyrazine derivatives in the literature, which are mainly divided into two types of synthesis methods. One is to for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/24
CPCC07D241/24
Inventor 夏晓峰赵明明何伟
Owner JIANGNAN UNIV