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A kind of preparation method of 2-quinolinone compound

A technology of quinolinones and compounds, which is applied in the field of preparation of pharmaceutical and chemical intermediates, and can solve problems such as harsh reaction conditions, cumbersome operations, and long reaction times

Active Publication Date: 2021-04-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally have problems such as long reaction time, cumbersome operation, and harsh reaction conditions.

Method used

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  • A kind of preparation method of 2-quinolinone compound
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  • A kind of preparation method of 2-quinolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]Example 1: Synthesis of 2-quinolinone (1a)

[0030]

[0031]Accurately weighed the reaction substrate quinoline-N-oxide (145.2 mg, 1.0 mmol) and zinc iodide (5 mol%, 15.9 mg) to add in the quartz reactor, adding acetonitrile 2.0mL, under air conditions, placed in a xenon lamp. After the reaction was illuminated, the acetonitrile was removed by a rotary evaporator, and purified by silica gel column (Oil ether: ethyl acetate = 2: 1) to obtain the reaction product. The product was a white powder solid, yield was 90% (130.7 mg).1H NMR (400MHz, DMSO) δ 11.72 (S, 1H), 7.86 (D, J = 9.5 Hz, 1H), 7.70-7.57 (m, 1H), 7.54-7.41 (m, 1H), 7.29 (D, J = 8.2Hz, 1H), 7.19-7.05 (m, 1H), 6.47 (D, J = 9.5 Hz, 1H).

Embodiment 2

[0032]Example 2: Synthesis of 6-methoxy-2-quinolinone (1b)

[0033]

[0034]Accurately weigh the reaction substrate 6-methoxyquinoline-N-oxide (175.1 mg, 1.0 mmol) and zinc oxide (3 mol%, 2.4 mg), add 2.0 ml of diethyl ether, under air conditions. After 2 h then reacting under a xenon lamp, diethyl ether was removed by a rotary evaporator, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2: 1) was obtained. The product was a white powder solid with a yield of 95% (166.3 mg).1H NMR (400 MHz, DMSO) δ11.62 (S, 1H), 7.83 (D, J = 9.5 Hz, 1H), 7.20 (DD, J = 13.8, 5.8 Hz, 1H), 7.13 (DD, J = 8.9, 2.8Hz, 1H), 6.47 (D, J = 9.5 Hz, 1H), 3.76 (s, 1h).

Embodiment 3

[0035]Example 3: Synthesis of 3-bromo-2-quinolinone (1C)

[0036]

[0037]

[0038]Accurately weighed 3-broncamin-N-oxide (223.0 mg, 1.0 mmol) and zinc bromide (1 mol%, 2.3 mg) were added to the quartz reactor, and 0.5 ml of toluene was added, and under air conditions, After the xenon lamp was taken for 3 h, the toluene was removed by a rotary evaporation instrument, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2: 1) obtained the reaction product. The product was a white powder solid, a yield of 90% (154.4 mg).1H NMR (400MHz, DMSO) δ12.28 (S, 1H), 8.68 (D, J = 2.6 Hz, 1H), 8.31 (DD, J = 9.1, 2.6 Hz, 1H), 8.11 (D, J = 9.6 Hz 1H), 7.41 (D, J = 9.1 Hz, 1H), 6.65 (DD, J = 9.6, 1.5 Hz, 1H).

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Abstract

The present invention provides a kind of preparation method of 2-quinolinone compound, take quinoline-N-oxide compound as raw material, take zinc salt as catalyst, react in organic solvent under xenon lamp illumination condition, synthesize a series of 2 ‑Quinolinones. The beneficial effect of the invention is that the quinolinone compound, as an important nitrogen-containing heterocyclic compound, has been applied to fields such as medicine and important reaction intermediates, and has broad market applications. The invention uses quinoline-N-oxide as raw material and cheap metal salt as a catalyst to react in an organic solvent under light conditions to synthesize a series of 2-quinolinone compounds. The patented method of the invention has simple steps and easy-to-obtain raw materials , mild reaction conditions, and meet the principles of green chemistry. The invention has great use value and social and economic benefits.

Description

Technical field[0001]The present invention relates to a method of preparing a pharmaceutical chemical intermediate, and a synthetic method of 2-quinolinone and a derivative thereof is specifically involved.Background technique[0002]2-quinolinone compounds are used as an important nitrogen-containing heterocyclic compound, which has been applied to the fields of medicine, important reaction intermediates, and with the development of science, 2-quinolinone and their derivatives have developed A variety of synthetic methods, including conventional Friedlander reactions, palladium-catalyzed CC coupling reaction synthesis of quinolinone, solid phase synthesis, microwave synthesis, etc. in recent years. However, these methods generally have problems with long reaction time, cumbersome operation, and harsh reaction conditions. Therefore, the development of simple development of 2-quinolinone compounds is one of the current research hotspots in the field of organic synthesis.[0003](1) Fried...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 于晓强包明冯秀娟杨萨娜
Owner DALIAN UNIV OF TECH
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