1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and preparation method thereof

A thiopyrimidine-based, ferrocene-based technology, applied in chemical instruments and methods, metallocenes, chemicals for biological control, etc., can solve the problems of large solvent usage, long reaction time, low yield, etc. , to achieve the effect of short reaction time, simple reaction process and simple post-processing

Inactive Publication Date: 2015-04-22
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Based on this, there is no literature report on the synthesis of a series of Michael addition products by grinding method.
Moreover, the preparation of existing ketone compounds is mostly based on the liquid phase reflux method, which has the disadvantages of long reaction time, low yield, and large solvent usage.

Method used

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  • 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Weigh 0.0012mol thiobarbituric acid, 0.0012mol anhydrous K 2 CO 3 Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-phenylpropenone, mix and grind. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with water, filter, and dry to obtain a dark red solid, which is 1-ferrocene Base-3-phenyl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-propanone. Yield 75%, m.p. 127°C-129°C.

[0059] IR (KBr tablet, v / cm -1 ):3440, 2921, 1782, 1715, 1646, 1595, 1494, 1450, 1073;

[0060] 1 H-NMR: 7.14-7.85 (m, 5H, Ar-H), 6.70 (s, 1H, -CONH), 4.95 (s, 2H, C 5 h 4 ), 4.63 (s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 2.03(d,2H,-COCH 2 ), 1.70(m, 1H, -CH);

[0061] 13 C-NMR: 192.5, 140.4, 134.7, 128.5, 127.8, 122.5, 43.1, 28.9.

Embodiment 2

[0063] Weigh 0.0012mol thiobarbituric acid, 0.0012mol anhydrous K 2 CO 3 Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-(p-chlorophenyl)-propenone, mix and grind. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with water, filter, and dry to obtain a dark red solid, which is 1-ferrocene Base-3-(p-chlorophenyl)-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-propanone. Yield 76%, m.p. 150°C-151°C.

[0064] IR (KBr tablet, v / cm -1 ):3420, 2920, 1783, 1715, 1646, 1598, 1450, 1077;

[0065] 1 H-NMR: 7.12-7.77 (m, 4H, Ar-H), 6.72 (s, 1H, -CONH), 4.94 (s, 2H, C5H 4 ), 4.64(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 2.05(d,2H,-COCH 2 ), 1.65(m, 1H, -CH);

[0066] 13 C-NMR: 192.8, 138.9, 135.7, 134.2, 128.9, 122.9, 43.8, 30.2.

Embodiment 3

[0068] Weigh 0.0012 mol of thiobarbituric acid and 0.0012 mol of NaOH in a mortar and mix quickly and uniformly, then add 0.001 mol of 1-ferrocenyl-3-(p-bromophenyl)-propenone, mix and grind. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with water, filter, and dry to obtain a dark red solid, which is 1-ferrocene Base-3-(p-bromophenyl)-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-propanone. Yield 73%, m.p. 159°C-160°C.

[0069] IR (KBr tablet, v / cm -1 ):3437, 2925, 1788, 1712, 1648, 1589, 1450, 1069;

[0070] 1 H-NMR: 7.16-7.57 (m, 4H, Ar-H), 6.71 (s, 1H, -CONH), 4.94 (s, 2H, C 5 h 4 ), 4.63 (s, 2H, C 5 h 4 ), 4.24(s, 5H, C 5 H5), 2.02(d,2H,-COCH 2 ), 1.65(m, 1H, -CH);

[0071] 13 C-NMR: 192.8, 139.7, 136.5, 131.7, 129.2, 122.8, 43.9, 31.0.

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and a preparation method thereof. The structural formula of the 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone is shown in the specification. The preparation method comprises the following steps: adding A mol of 1-ferrocenyl-3-aryl-acrylketone, B mol of anhydrous K2CO3 (or NaOH) and C mol of thiobarbituric acid into a dried mortar, grinding the materials fast, performing TLC tests till complete reaction, and then performing washing, suction filtration and drying to obtain the 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone. The invention has the advantages that the 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and the preparation method thereof are provided, and the method has short reaction time, does not need a solvent, is green, environment-friendly and economic, is simple to operate, moderate in reaction condition and simple in after-treatment and has high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-(2,6-dicarbonyl-4-thiopyrimidinyl)-acetone and a preparation method thereof. Background technique [0002] In organic chemistry, the conjugated addition of carbanions to a, β-unsaturated conjugated systems (aldehydes, ketones, esters, nitriles and nitro compounds, etc.) is called Michael (Michael) addition reaction. Usually, the compound that can form nucleophilic carbanion is called donor, and the electrophilic α, β-unsaturated conjugated system is called acceptor. Generally expressed by the following general formula: [0003] [0004] Among them, y represents an electron-withdrawing group that can be conjugated with C=C, such as -CHO, -COR, -COOR, -CN and -NO2, etc.; HR represents a compound containing active hydrogen, which is a donor, including Lewis protonic acid , aldehydes, ketones or esters containing a-H and substances with electron...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A01P1/00A61P31/00
CPCC07F17/02
Inventor 尹大伟宋思梦刘玉婷杨阿宁王金玉刘蓓蓓尹静怡吴倩倩
Owner SHAANXI UNIV OF SCI & TECH
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