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The synthetic method of quinoline oxide

A synthesis method and oxide technology, applied in organic chemistry and other directions, can solve problems such as uneconomical, unfriendly environment, unsatisfactory product yield, etc., and achieve the effects of high yield, simple reaction system and short reaction time.

Inactive Publication Date: 2020-06-26
QINGDAO AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in the above-mentioned preparation process, the metal catalyst used is expensive, and the environment is not friendly, and the yield of the obtained product is not ideal, etc.
Therefore, the method currently provided is not economical, nor is it the optimal solution in the experimental synthesis of quinoline oxides.

Method used

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  • The synthetic method of quinoline oxide
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  • The synthetic method of quinoline oxide

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preparation example Construction

[0023] The embodiment of the present invention provides a synthesis method of quinoline oxides, comprising the following steps:

[0024] S1: add quinoline 1-oxide compound and semicarbazide compound respectively into the reactor, under the action of sodium persulfate and solvent, seal and react at 80-100°C in air for 2-10 hours;

[0025] In this step, quinoline 1-oxide compounds and semicarbazide compounds are used to synthesize quinoline oxides. Specifically, semicarbazide compounds generate acyl radicals under the action of sodium persulfate, and then acyl radicals React with nitrogen oxides, and finally leave the hydrogen atom to generate the target product. What needs to be explained here is that this step can be completed without using a metal catalyst, and the reaction can be completed by using cheap and easily available sodium persulfate oxidant; in addition, the method has good selectivity, and the product yield can be as high as 97%. It can be understood that the rea...

Embodiment 1

[0042] Add to the reactor separately 1mmol, 1mmol, 2mmol of sodium persulfate, 2ml of water, sealed and reacted at 100°C for 2 hours in the air, and separated by column chromatography after the reaction to obtain the target compound P1:

[0043]

[0044] Carry out nuclear magnetic spectrum analysis to above-mentioned yellow solid powder, data is as follows:

[0045] 1 H NMR (500MHz, CDCl 3 )δ13.82(s,1H),8.74(d,J=8.7Hz,1H),8.42(d,J=8.8Hz,1H),7.97–7.72(m,5H),7.66(t,J=7.2 Hz, 1H), 7.31(t, J=7.3Hz, 2H), 7.10(t, J=7.1Hz, 1H);

[0046] 13 C NMR (126MHz, CDCl 3 )δ158.04, 141.63, 137.83, 137.67, 131.47, 130.81, 130.04, 129.10, 128.34, 127.04, 124.98, 122.66, 121.15, 120.17;

[0047] After identification, the spectral data corresponds to the structural formula, proving that the synthesized product is 2-(phenylcarbamoyl)quinoline 1-oxide, and the yield is 97%.

Embodiment 2

[0049] Add to the reactor separately 1mmol, 1mmol, 2mmol of sodium persulfate, 2ml of water, sealed and reacted at 80°C for 6 hours in the air, and separated by column chromatography after the reaction to obtain the target compound P2:

[0050]

[0051] Carry out nuclear magnetic spectrum analysis to above-mentioned yellow solid powder, data is as follows:

[0052] 1 H NMR (500MHz, CDCl 3)δ13.73(s,1H),8.79(d,J=8.8Hz,1H),8.47(d,J=8.9Hz,1H),8.34(d,J=8.0Hz,1H),7.87(t, J=7.8Hz, 2H), 7.80(t, J=7.8Hz, 1H), 7.69(t, J=7.5Hz, 1H), 7.21(dd, J=14.0, 7.5Hz, 2H), 7.05(t, J=7.4Hz, 1H), 2.43(s, 3H);

[0053] 13 C NMR (126MHz, CDCl 3 )δ158.03, 141.66, 138.05, 136.42, 131.38, 130.81, 130.40, 130.01, 128.71, 128.31, 126.98, 126.72, 124.96, 122.78, 122.10, 120.31, 18.58;

[0054] After identification, the spectral data corresponds to the structural formula, proving that the synthesized product is 2-(o-tolylcarbamoyl)quinoline 1-oxide, and the yield is 96%.

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Abstract

The invention provides a synthesis method of quinoline oxide, and belongs to the field of organic synthesis. According to the synthesis method, no metal catalysts need to be used, reaction can be completed only by using a sodium persulfate oxidizing agent which is cheap and easy to obtain, and a reaction system is simple and high in yield. According to the technical scheme, the synthesis method ofthe quinoline oxide comprises the steps of adding a quinoline 1-oxide compound and a semi carbazide compound into a reactor separately, and under the action of sodium persulfate and a solvent, carrying out sealed reaction for 2-10 hours under a condition of 80-100-DEG C air; and after the reaction is completed, conducting column chromatography separation to obtain the quinoline oxide. The provided synthesis method can provide an optimal alternative solving scheme for efficiently synthesizing the quinoline oxide.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a synthesis method of quinoline oxides. Background technique [0002] Quinoline oxides have a variety of biological activities, and have achieved satisfactory multi-faceted effects in recent years, and have attracted more and more attention from chemical researchers all over the world. At present, the existing quinoline oxides that can be used are prepared by using quinoline 1-oxide and N-diphenylhydrazine to react at high temperature in the presence of an oxidizing agent with an expensive metal catalyst. (Adv. Synth. Catal., 2019, 361). [0003] However, in the above-mentioned preparation process, the metal catalyst used is expensive, and the environment is not friendly, and the yield of the obtained product is not ideal. Therefore, the method currently provided is not economical, nor is it the optimal solution in the experimental synthesis of quinoline oxides. Contents of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/60
CPCC07D215/60
Inventor 王祖利李光辉陈德茂韩晴晴孙媛媛吴琼
Owner QINGDAO AGRI UNIV