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Synthesis method and application of imidazole derivative

A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of poor tolerance of functional groups, complex and difficult to obtain raw materials, long reaction time, etc., and achieve the effect of scientific and reasonable synthesis method, convenient development and application, and cheap raw materials

Active Publication Date: 2016-08-17
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as complex and difficult to obtain raw materials, long reaction time, low yield, poor tolerance of functional groups, etc.

Method used

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  • Synthesis method and application of imidazole derivative
  • Synthesis method and application of imidazole derivative
  • Synthesis method and application of imidazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1——compound shown in preparation formula IIIa (R 1 =R 2 =Cy, R 3 =R 4 =H):

[0041]

[0042]At room temperature, add 1.05 mmol of ethyl glycine hydrochloride, 1.05 mmol of triethylamine and 0.05 mmol of zinc trifluoromethanesulfonate into a 25 mL reaction tube, and add 5 mL of benzene to dissolve. Then add 1.0 mmol of N,N'-dicyclohexylcarbodiimide, and react at 80°C for 8 hours. The reaction system is a yellow suspension. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether:ethyl acetate=6:1 was used as an eluent to obtain 239 mg of imidazolone derivative (IIIa) (purity>98%, yellow solid), and the isolated yield was 91%.

[0043] The NMR data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ): δ1.24(d, J=6.2Hz, 6H, CH 3 ), 1.42, (d, J=7.0Hz, 6H, CH 3 ),3.92(s,2H,CH 2 ),4.13-4.25(m,2H,CH); 13 C NMR (100MHz, CDCl 3 ): δ19.73, 22.85, 43.56, 55.76, 60.09, 155.35, 1...

Embodiment 2

[0044] Embodiment 2——compound shown in preparation formula IIIb (R 1 =R 2 = 4-MeC 6 h 4 , R 3 =R 4 =H):

[0045]

[0046] At room temperature, add 1.05 mmol of ethyl glycine hydrochloride, 1.05 mmol of triethylamine and 0.05 mmol of zinc trifluoromethanesulfonate into a 25 mL reaction tube, and add 5 mL of benzene to dissolve. Then add 1.0 mmol of N,N'-di-p-methylphenylcarbodiimide, and react at 80°C for 8 hours. The reaction system is a yellow suspension. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate=6:1 was used as an eluent to obtain 262 mg of imidazolone derivative (IIIb) (purity>98%, yellow solid), and the isolated yield 94%.

[0047] The NMR data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ):δ2.29(s,3H,CH 3 ),2.38(brs,3H,CH 3 ),3.90(brs,1H,CH 2 ),4.22(brs,1H,CH 2 ),4.38(brs,1H,NH),6.81-6.83(m,2H,CH),7.07-7.09(m,2H,CH),7.24-7.29(m,4H,CH); 13 C N...

Embodiment 3

[0048] Embodiment 3——compound shown in preparation formula IIIc (R 1 =Bn,R 2 =2,6- i PrC 3 h 6 , R 3 =R 4 =H):

[0049]

[0050] At room temperature, add 1.05 mmol of ethyl glycine hydrochloride, 1.05 mmol of 4-(N,N-dimethylamino)pyridine and 0.05 mmol of zinc trifluoromethanesulfonate to a 25 mL reaction tube, add 5 mL of benzene dissolve. Then 1.0 mmol of 1-benzyl-3-(2,6-diisopropylphenyl)diimine was added and reacted at 50° C. for 4 hours. The reaction system is a yellow suspension. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate=6:1 was used as an eluent to obtain 255 mg of imidazolone derivative (IIIc) (purity>98%, yellow solid), and the isolated yield was 71%.

[0051] The NMR data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ):δ1.08-1.10(m,12H,CH 3 ),2.82-2.89(m,2H,CH),3.85(s,2H,CH 2 ),4.25(brs,1H,NH),4.91(s,2H,CH 2 ),7.00-7.10(m,3H,CH),7.27-7.34...

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Abstract

The invention provides synthesis method and application of an imidazole derivative. The method uses carbodiimide, hydrochloride salt of amino-acid ester, tertiary amine and zinc triflate in a catalytic amount to prepare 2-amino or imino substituted imidazole derivative. The synthesis method is scientific and rational, provides a general method for synthesis of an imidazole derivative with a variety of substituents, and can further synthesize more complex heterocyclic molecules, such as benzimidazole imidazolone. The method has the advantages of easily available raw materials, wide range of application, high separation yield, simple laboratory equipment and operations, is convenient for further development and application; and the synthesized products have potential applications in biology, pharmacy and materials.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a series of nitrogen-containing heterocyclic compounds, especially the synthesis method and application of imidazolone derivatives. Background technique [0002] Guanidine compounds widely exist in organisms. For example, the essential amino acid arginine in the human body contains guanidine groups, and many nitrogen-containing heterocyclic compounds also have guanidine moieties, such as 2-aminoimidazolone derivatives. These molecules have applications in a wide range of fields such as chemistry, biology, pharmaceuticals, and materials engineering. [0003] As described below, the use of 2-aminoimidazolone compounds in various fields has been reported. [0004] "The Structure of Dibromoagelaspongin-A Novel Bromine-Containing Guani dine Derivative From the Marine Sponge Agelas sp. Tetrahedron 1989,45,3487", "Leucettines, a Class of Potent Inhibitors of cdc2-Like Kinases and Dual S...

Claims

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Application Information

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IPC IPC(8): C07D233/88C07D487/04
Inventor 张文雄迟樾席振峰
Owner PEKING UNIV
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