Method for preparing quinolones compound by using pentacarbonyl iron as CO release source

A technology of iron pentacarbonyl and quinolones is applied in the synthesis field of quinolones to achieve the effects of easy control, mild reaction conditions and high atom economy

Inactive Publication Date: 2018-09-21
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of quinolones, to provide a method for changing the source of CO, without adding ligands, with mild reaction conditions, short reaction time, single reaction product, safe and efficient, and high yield. The preparation method of quinolones compound

Method used

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  • Method for preparing quinolones compound by using pentacarbonyl iron as CO release source
  • Method for preparing quinolones compound by using pentacarbonyl iron as CO release source
  • Method for preparing quinolones compound by using pentacarbonyl iron as CO release source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Preparation of 2-phenylquinolin-1H-4-one with the following structural formula

[0014]

[0015] 0.1095g (0.5mmol) 2-iodoaniline, 66μL (0.60mmol) phenylacetylene, 0.0056g (0.025mmol) palladium acetate, 0.3184g (1.5mmol) potassium phosphate, 0.0431g (0.5mmol) piperazine and 34μL (0.25 mmol) of iron pentacarbonyl and 3mL of anhydrous acetonitrile were added to the Shrek tube, stirred and reacted at 50°C for 10 hours, the reaction was stopped, and the reaction was naturally cooled to room temperature, separated by column chromatography to obtain solid 2-phenylquinolin-1H-4-one , its yield is 86%, and the structural characterization data are: 1 H NMR (600MHz, DMSO) δ11.72(s, 1H), 8.11(dd, J=8.0, 0.9Hz, 1H), 7.87–7.82(m, 2H), 7.78(d, J=8.3Hz, 1H) ,7.71–7.65(m,1H),7.60(dd,J=4.9,1.5Hz,3H),7.35(t,J=7.4Hz,1H),6.34(s,1H); 13 CNMR(151MHz,DMSO)δ 176.93,150.14,140.61,134.25,131.76,130.39,128.96,127.38,124.78,124.67,123.29,118.85,107.25.

Embodiment 2

[0017] Preparation of 2-(4-methoxyphenyl)quinolin-1H-4-one with the following structural formula

[0018]

[0019] In Example 1, the phenylacetylene used was replaced with equimolar 4-methoxyphenylacetylene, and other steps were the same as in Example 1 to obtain solid 2-(4-methoxyphenyl)quinoline-1H-4- Ketone, its yield is 81%, and structural characterization data is: 1 H NMR (600MHz, DMSO) δ11.59(s, 1H), 8.09(d, J=7.9Hz, 1H), 7.79(dd, J=25.1, 8.3Hz, 3H), 7.65(t, J=7.5Hz ,1H),7.32(t,J=7.4Hz,1H),7.13(d,J=8.6Hz,2H), 6.31(s,1H),3.85(s,3H); 13 C NMR (151MHz, DMSO) δ176.83, 161.03, 149.68, 140.51, 131.59, 128.80, 126.26, 124.77, 124.64, 123.06, 118.60, 114.37, 106.47, 55.42.

Embodiment 3

[0021] Preparation of 2-(4-methylphenyl)quinolin-1H-4-one with the following structural formula

[0022]

[0023] In Example 1, the phenylacetylene used is replaced with equimolar 4-methylphenylacetylene, and other steps are the same as in Example 1 to obtain solid 2-(4-methylphenyl)quinolin-1H-4-one, Its yield is 84%, and structural characterization data is: 1 H NMR(600MHz,DMSO)δ11.65(s,1H),8.10(d,J=7.5Hz,1H),7.81–7.61(m,4H), 7.44–7.27(m,3H),6.32(s, 1H),2.40(s,3H); 13 C NMR(151MHz,DMSO)δ176.90, 149.88,140.50,140.31,131.69,131.28,129.51,127.20,124.85,124.68,123.13,118.64, 106.91,20.86.

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Abstract

The invention discloses a method for preparing quinolones compound by using pentacarbonyl iron as a CO release source. In this method, iron pentacarbonyl is used as a CO release source, and palladiumacetate is used as a catalyst, potassium phosphate and piperazine are used as a base, and acetonitrile is used as a solvent to couple a 2-iodoaniline compound with a terminal alkyne under mild conditions to obtain the quinolones compound. The preparation method has the advantages of simple operation, mild reaction conditions, less catalyst use, less CO release source use, low toxicity, lower cost,wide substrate applicability, and high target compound yield, and the method can be widely used for the preparation of natural quinolones compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis of quinolone compounds, in particular to a 5 As a carbon monoxide (CO) release source, 2-iodoaniline compounds are used as reaction substrates, and palladium acetate is used as a catalyst, potassium phosphate and piperazine as bases to synthesize quinolones under mild conditions without adding any ligands method of compounds. Background technique [0002] Quinolones are very important heterocyclic compounds with a wide range of biological activities and medicinal value, such as: anti-malarial, anti-virus, anti-inflammation, anti-cancer, etc. A core structure that is of great importance in organic synthesis. Therefore, it has attracted extensive attention in the fields of organic synthesis and pharmaceuticals. [0003] There are many ways to synthesize this compound, palladium catalyzed carbonylation method is a convenient and efficient method. In the early days, CO gas was usually used as th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/233C07D409/04
CPCC07D215/233C07D409/04
Inventor 高子伟马富余徐珊张伟强孙华明张国防
Owner SHAANXI NORMAL UNIV
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