Method for synthesizing 3,4-dihydropyrimidine-2-one derivative

A technology for dihydropyrimidine and derivatives, applied in the field of synthesizing 3,4-dihydropyrimidin-2-one derivatives, which can solve the problems of difficult recovery and high recovery cost

Inactive Publication Date: 2016-06-29
TAIZHOU UNIV
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  • Abstract
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Problems solved by technology

[0004] In order to increase the yield of the reaction and shorten the reaction time, people have done a lot of research work on catalyst screening and found that FeCl 3 ·6H 2 O (Organic Chemistry, 2000, 20, 815), NiCl 2 .6H 2 Catalysts such as O (Organic Chemistry, 2002, 22, 788) can synthesize 3,4-dihydropyrimidinone compounds in higher yields, but due to their good water solubility, these catalysts are soluble in water during the post-treatment process and are difficult to recycle. High recycling cost

Method used

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  • Method for synthesizing 3,4-dihydropyrimidine-2-one derivative
  • Method for synthesizing 3,4-dihydropyrimidine-2-one derivative
  • Method for synthesizing 3,4-dihydropyrimidine-2-one derivative

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Embodiment 1

[0027] In a 50 mL round bottom flask, add benzaldehyde (3.0 mmol), ethyl acetoacetate (3.0 mmol), urea (3.6 mmol), 4 mL ethanol, magnetic nanoparticles supported SnCl 2 Catalyst 0.3g, reacted at a reaction temperature of 75°C for 5h. After judging by thin-layer chromatography that the reaction is complete, the catalyst is held by a magnet, and the reaction solution is poured out while it is hot. After cooling to room temperature, 10 mL of cold water was added to precipitate a solid. Filter, wash the solid with 3 mL of cold ethanol, and recrystallize the solid with ethanol. 0.751 g of 4-phenyl-6-methyl-5-(ethoxycarbonyl)-3,4-dihydropyrimidin-2-one was obtained, with a yield of 96.2% and a content of 95.6%. 1 HNMR(DMSO-d6)δ: 9.17(s,1H),7.72(s,1H),7.32(t,2H,J=7.2Hz),7.23-7.25(m,3H),5.14(d,1H,J =3.2Hz), 3.96-4.01(m, 2H), 2.25(s, 3H), 1.09(t, 3H, J=7.2Hz); 13 CNMR(DMSO-d6)δ: 165.81, 152.58, 145.34, 128.84, 127.71, 126.71, 99.77, 59.63, 54.44, 18.23, 14.54.

Embodiment 2

[0029] In a 50 mL round bottom flask, add 3-nitrobenzaldehyde (3.0 mmol), ethyl acetoacetate (3.0 mmol), urea (3.6 mmol), 4 mL ethanol, magnetic nanoparticles supported SnCl 2 Catalyst 0.3g was reacted at a reaction temperature of 75°C for 7h. Use thin-layer chromatography to judge that the reaction is complete, use a magnet to hold the catalyst, and pour out the reaction solution while it is hot. After cooling to room temperature, 10 mL of cold water was added to precipitate a solid. Filter, wash the solid with 3 mL of cold ethanol, and recrystallize the solid with ethanol. 0.806 g of 4-(3-nitrophenyl)-6-methyl-5-(ethoxycarbonyl)-3,4-dihydropyrimidin-2-one was obtained, with a yield of 88.0% and a content of 97.0%. 1 HNMR(DMSO-d6)δ: 9.37(s,1H), 8.10-8.15(m,2H), 7.91(s,1H), 7.64-7.72(m,2H), 5.32(d,1H, J=3.2Hz ),4.00-4.02(m,2H),2.29(s,3H),1.11(s,3H); 13 CNMR(DMSO-d6)δ: 165.53, 152.25, 149.87, 148.24, 147.47, 133.45, 130.67, 122.79, 121.48, 98.84, 59.85, 54.04, 18.31, 14.46....

Embodiment 3

[0031] In a 50 mL round bottom flask, add 2-chlorobenzaldehyde (3.0 mmol), ethyl acetoacetate (3.0 mmol), urea (3.6 mmol), 4 mL ethanol, magnetic nanoparticles supported SnCl 2 Catalyst 0.3g, reacted at a reaction temperature of 75°C for 6h. Use thin-layer chromatography to judge that the reaction is complete, use a magnet to hold the catalyst, and pour out the reaction solution while it is hot. After cooling to room temperature, 10 mL of cold water was added to precipitate a solid. Filter, wash the solid with 3 mL of cold ethanol, and recrystallize the solid with ethanol. 0.778 g of 4-(2-chlorophenyl)-6-methyl-5-(ethoxycarbonyl)-3,4-dihydropyrimidin-2-one was obtained, with a yield of 88.0% and a content of 96.7%. 1 HNMR (DMSO-d6) δ: 9.25(s, 1H), 7.68(s, 1H), 7.39(d, 1H, J=7.6Hz), 7.31(t, 2H, J=3.6Hz), 7.26(d, 1H, J=7.6Hz), 5.63(d, 1H, J=3.2Hz), 3.87-3.92(m, 2H), 2.30(s, 3H), 0.99(t, 3H, J=7.2Hz); 13CNMR(DMSO-d6)δ: 165.43, 151.77, 149.73, 142.19, 132.17, 129.82, 129.52, 1...

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Abstract

The invention relates to an efficient and environment-friendly catalyst. On the mild reaction condition, a method for synthesizing 3,4-dihydropyrimidine-2-one derivative in a one-pot mode is achieved. The method comprises the steps that magnetic nano-particle load SnCl2 is adopted as a catalyst, ethyl alcohol is adopted as a reaction medium, and the three components of aldehyde, an alpha, beta-dicarbonyl compound and urea (thiourea) are condensed in a one-pot mode to obtain the 3,4-dihydropyrimidine-2-one derivative. The magnetic nano-particle load SnCl2 is repeatedly adopted seven times, and the catalytic reaction yield is not lowered obviously. The method is easy to implement, high in yield, short in reaction time, mild in reaction condition and wide in industrial application prospect, and the reusability of a catalytic reaction system is good.

Description

technical field [0001] The invention relates to a high-efficiency, green, SnCl loaded with magnetic nanoparticles 2 The catalyst is a method for synthesizing 3,4-dihydropyrimidin-2-one derivatives in a "one-pot method". technical background [0002] 3,4-Dihydropyrimidinone compounds are a class of important biologically active substances, which have many important pharmacological effects, such as anti-virus, anti-infection, anti-cancer, anti-bacterial, pain relief and anti-inflammatory, etc., and can be used as calcium antagonists, Antihypertensive agents, α-antagonists, can also be used as a lead in the development of anticancer drugs. As early as 1893, Biginelli used benzaldehyde, ethyl acetoacetate, and urea to obtain such compounds for the first time under the catalysis of hydrochloric acid (Gazz.Chim.Ital.1893,23,360). This synthetic method is called Biginelli reaction. However, there are problems such as long reaction time (18h) and low yield (20-50%) in this method....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/22B01J27/128B01J35/02
CPCC07D239/22B01J27/128B01J35/0033
Inventor 黄孟君应安国吴海燕蒋慧丹吕晓飒
Owner TAIZHOU UNIV
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