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The synthetic method of quinoline compound containing sulfonyl group

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve problems such as uneconomical, unfriendly to the environment, and unsatisfactory product yields, and achieve the effects of high reaction yield, simple reaction system, and high product yield

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

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Problems solved by technology

[0003] However, in the above-mentioned preparation process, not only catalysts are used in the reaction system, but also high temperature heating is required, which makes the environment unfriendly, and the yield of the obtained products is not ideal, etc.
Therefore, the method currently provided is not economical, nor is it the optimal solution in the experimental synthesis of sulfonyl-containing quinoline compounds.

Method used

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  • The synthetic method of quinoline compound containing sulfonyl group
  • The synthetic method of quinoline compound containing sulfonyl group
  • The synthetic method of quinoline compound containing sulfonyl group

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preparation example Construction

[0022] The embodiment of the present invention provides a synthetic method of quinoline compounds, comprising the following steps:

[0023] S1: Add quinoline compounds and sulfonyl chloride compounds to the reactor respectively, under the action of photocatalyst and solvent acetone, react at room temperature for 4-12 hours under the condition of white LED light;

[0024] In this step, quinoline compounds and sulfonyl chloride compounds are used to synthesize sulfonyl-containing quinoline compounds. Specifically, benzophenone is excited under light conditions to become oxygen free radicals, and then capture quinoline The hydrogen atom at the benzylic position of the analogous compound generates a carbon free radical, and the next step reacts with sulfonyl chloride to generate the target product. What needs to be explained here is that the reaction in this step does not need to be heated, and the reaction can be carried out at room temperature. The amount of benzophenone used as...

Embodiment 1

[0039] Add to the reactor separately 1mmol, 1mmol of benzenesulfonyl chloride, 0.1mmol of benzophenone, and 2ml of acetone were reacted at room temperature for 4 hours under the condition of white 8W LED light. After the reaction, the target compound C1 was obtained by column chromatography:

[0040]

[0041] Carry out nuclear magnetic spectrum analysis to above-mentioned white solid powder, data is as follows:

[0042] 1 H NMR (500MHz, CDCl3) δ8.06(d, J=8.4Hz, 1H), 7.75(d, J=8.5Hz, 1H), 7.71(d, J=8.1Hz, 1H), 7.62–7.53(m ,3H),7.46(t,J=9.8Hz,3H),7.30(t,J=7.8Hz,2H),4.67(s,2H);

[0043] 13 C NMR (126MHz, CDCl 3 )δ149.25s, 147.80, 138.30, 136.97, 133.82, 129.93, 129.11, 128.97, 128.52, 127.61, 127.36, 127.21, 122.76, 65.14;

[0044] After identification, the spectrum data corresponds to the structural formula, proving that the synthesized product is 2-((phenylsulfonyl)methyl)quinoline with a yield of 97%.

Embodiment 2

[0046] Add to the reactor separately 1mmol, 1.1mmol of benzenesulfonyl chloride, 0.1mmol of benzophenone, and 2ml of acetone were reacted at room temperature for 6 hours under white 8W LED light. After the reaction, the target compound C2 was obtained by column chromatography:

[0047]

[0048] Carry out nuclear magnetic spectrum analysis to above-mentioned white solid powder, data is as follows:

[0049] 1 H NMR (500MHz, CDCl 3)δ8.04(d, J=8.4Hz, 1H), 7.73(s, 1H), 7.65(d, J=8.7Hz, 1H), 7.59(d, J=7.9Hz, 2H), 7.49(dd, J=15.2, 7.9Hz, 2H), 7.39(d, J=8.7Hz, 1H), 7.34(t, J=7.6Hz, 2H), 4.63(s, 2H);

[0050] 13 C NMR (126MHz, CDCl 3 )δ150.44, 148.13, 138.20, 136.72, 135.76, 133.96, 129.05, 128.85, 128.47, 128.26, 128.18, 125.68, 122.96, 65.12;

[0051] After identification, the spectral data corresponded to the structural formula, proving that the synthesized product was 7-chloro-2-(phenylsulfonyl)methyl)quinoline with a yield of 92%.

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Abstract

The invention provides a synthesis method of a sulfonyl-containing quinoline compound, 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 under the action of a visible-light-induced photocatalyst, a reaction system is simple, heating is not needed in the reaction, and the reaction yield is high. According to the technical scheme, the synthesis method of the sulfonyl-containing quinoline compound comprises the steps of adding a quinoline compound and a sulfonyl chloride compound into a reactor separately, and under the action of the photocatalyst and a solvent acetone, carrying out room-temperature reaction for 4-12 hours under a condition of white LED lamp illumination; and after the reactionis completed, conducting column chromatography separation to obtain the sulfonyl-containing quinoline compound. The provided synthesis method provides an optimal alternative solving scheme for efficiently synthesizing the sulfonyl-containing quinoline compound.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing sulfonyl-containing quinoline compounds. Background technique [0002] Sulfonyl-containing quinoline compounds 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 available preparation method of quinoline compounds containing sulfonyl groups is that quinoline compounds and sodium benzenesulfonate are prepared by reacting under high temperature conditions in the presence of iodine catalyst and oxidizing agent (Chem.Commun., 2015, 51, 652). [0003] However, in the above-mentioned preparation process, not only a catalyst is used in the reaction system, but also high temperature heating is required, which makes the environment unfriendly, and the yield of the obtained product is not ide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/12C07D215/18
CPCC07D215/12C07D215/18
Inventor 王祖利李光辉陈德茂韩晴晴孙媛媛吴琼
Owner QINGDAO AGRI UNIV