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

A pyrimidinetrione-based and ferrocenyl-based technology, applied in the field of 1-ferrocenyl-3-aryl-3--acetone and its preparation, can solve the problem of low yield, long reaction time and solvent usage Large volume and other problems, to achieve the effect of simple reaction process, short reaction time and low equipment requirements

Inactive Publication Date: 2015-05-06
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057]Weigh 0.0012mol barbituric 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 pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-phenyl-3-(2,4,6-pyrimidintrionyl)-propanone. m.p.131°C~132°C.

[0058] IR (KBr tablet, v / cm -1 ):3416, 2933, 1700, 1659, 1599, 1553, 1494, 1450, 1251;

[0059] 1 H-NMR: 7.15-7.85 (m, 5H, Ar-H), 5.34 (s, 1H, -CONH-), 4.80 (s, 2H, C 5 h 4 ), 4.54(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 3.10 (d, 2H, -COCH 2 ), 1.70(m, 1H, -CH);

[0060] 13 C-NMR: 192.8, 140.4, 134.7, 128.5, 127.8, 122.5, 44.2, 29.0.

Embodiment 2

[0062] Weigh 0.0012mol barbituric 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 pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-chlorophenyl)-3-(2,4,6-pyrimidintrionyl)-propanone. m.p.155°C~156°C.

[0063] IR (KBr tablet, v / cm -1 ):3398, 2931, 1707, 1661, 1595, 1491, 1453, 1256;

[0064] 1 H-NMR: 7.13-7.76 (m, 4H, Ar-H), 6.05 (s, 1H, -CONH-), 4.94 (s, 2H, C 5 h 4 ), 4.64(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 3.10 (d, 2H, -COCH 2 ), 1.66(m, 1H, -CH);

[0065] 13 C-NMR: 192.5, 138.9, 136.5, 134.8, 128.9, 128.7, 122.9, 43.9, 30.2.

Embodiment 3

[0067] Weigh 0.0012mol barbituric acid, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and uniformly, then add 0.001mol 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 pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-bromophenyl)-3-(2,4,6-pyrimidintrionyl)-propanone. m.p.171°C~172°C.

[0068] IR (KBr tablet, v / cm -1 ):3414, 2922, 1707, 1659, 1563, 1486, 1450, 1254;

[0069] 1 H-NMR: 7.11-7.76 (m, 4H, Ar-H), 6.01 (s, 1H, -CONH-), 4.93 (s, 2H, C 5 h 4 ), 4.64(s, 2H, C 5 h 4 ), 4.24(s, 5H, C 5 h 5 ), 3.09 (d, 2H, -COCH 2 ), 1.70(m, 1H, -CH);

[0070] 13 C-NMR: 192.5, 138.9, 134.5, 131.7, 129.2, 123.5, 122.9, 42.5, 31.5.

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetriketo)-acetone and a preparation method thereof. 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetriketo)-acetone has a structural formula as shown in the description. The preparation method comprises the following steps: adding A mol of 1-ferrocene-3-aryl-propenone, B mol of anhydrous K2CO3 (or NaOH) and C mol of barbituric acid into a dried mortar, rapidly grinding, detecting with TLC until the reaction is completed, washing with water, carrying out suction-filtration and drying to obtain 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetriketo)-acetone. The 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetriketo)-acetone and the preparation method thereof have the advantages that the method is simple in operation and post-treatment, mild in reaction conditions and high in yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetrionyl)-acetone and a preparation method thereof. Background technique [0002] The solvent-free Michael addition reaction has the advantages of high yield, strong selectivity, simple operation and low cost, and is especially beneficial to the protection of the environment. Under solvent-free conditions, using various alkaline and acidic catalysts with high catalytic efficiency, cheap and easy to obtain, or even without any catalyst, can effectively avoid condensation, rearrangement, polymerization and other side reactions. [0003] The research on the application of grinding method in solid-phase organic synthesis has developed very rapidly in the past 20 or 30 years. It is more convenient and easy to operate than traditional organic synthesis methods. Many traditional reactions can be carried out under milder conditions under g...

Claims

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Application Information

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IPC IPC(8): C07F17/02A01P1/00A01P3/00A01P13/00
CPCC07F17/02
Inventor 刘玉婷宋思梦尹大伟尹静怡王金玉杨阿宁刘蓓蓓黄涛
Owner SHAANXI UNIV OF SCI & TECH
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