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Synthesis method for multi-substituted 2-imidoimidazoline-4,5-diketone

A technology of imide imidazoline and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of large method limitation, limited change of substituents, large environmental pollution, etc., and achieves a wide range of application, high yield and easy-to-obtain raw materials. Effect

Inactive Publication Date: 2012-07-04
PEKING UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, there are only sporadic reports on the synthesis methods of 2-iminoimidazoline-4,5-dione derivatives provided by domestic and foreign literature, and the method limitations are relatively large
For example, starting from 1-methylhydantoin-2-imide, 2-iminoimidazoline-4,5-dione is synthesized by oxidizing 5-methylene into carbonyl with an oxidizing agent such as mercury acetate, Not only is the change of substituents limited, but the oxidant that needs to be used in the reaction also pollutes the environment greatly, so the limitations of traditional methods are relatively large

Method used

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  • Synthesis method for multi-substituted 2-imidoimidazoline-4,5-diketone
  • Synthesis method for multi-substituted 2-imidoimidazoline-4,5-diketone
  • Synthesis method for multi-substituted 2-imidoimidazoline-4,5-diketone

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Experimental program
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Effect test

Embodiment 3

[0036] Embodiment 3——compound shown in preparation formula IVc (R 1 = R 2 = i Pr, R 3 =3-HCC-C 6 h 4 ):

[0037]

[0038] Under nitrogen protection, 1 mmol N,N'-diisopropylcarbodiimide and 1.1 mmol oxalyl chloride were added to a 20 mL reaction tube containing 3 mL of ether, and reacted at 25°C for 1 hour. The reaction gradually precipitated a white solid. Add 3 mL of tetrahydrofuran to the reaction system to dissolve the solid, then add 1.1 mmol of 3-aminophenylacetylene and 2.0 mmol of triethylamine, and react at 25°C for 12 hours. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate = 10:1 (v / v) was used as the eluent to obtain 1,3-diisopropyl-2-(3-ethynyl Phenyl)iminoimidazoline-4,5-dione 211 mg (purity>98%, yellow solid), isolated yield 71%. The NMR data of this compound are as follows: 1 H NMR (300MHz, CDCl 3 , Me 4 Si): δ1.38 (d, J=6.9Hz, 12H, CH 3 ), 3.10(s, 1H, CH...

Embodiment 5

[0042] Embodiment 5——compound shown in preparation formula IVe (R 1 = R 2 = i Pr, R 3 =4-methylthiazol-2-yl):

[0043]

[0044] Under nitrogen protection, 1 mmol N,N'-diisopropylcarbodiimide and 1.1 mmol oxalyl chloride were added to a 20 mL reaction tube containing 3 mL of ether, and reacted at 25°C for 1 hour. The reaction gradually precipitated a white solid. Add 3mL tetrahydrofuran to the reaction system to dissolve the solid, then add 1.1mmol 4-methyl 2-aminothiazole and 2.0mmol triethylamine, and react at 25°C for 12 hours. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether: ethyl acetate = 10:1 (v / v) was used as the eluent to obtain 1,3-diisopropyl-2-(4-methyl Thiazol-2-yl)iminoimidazoline-4,5-dione 159 mg (purity>98%, orange solid), isolated yield 54%. The NMR data of this compound are as follows: 1 H NMR (300MHz, CDCl 3 , Me 4 Si): δ1.45 (d, J=6.9Hz, 12H, CH 3 ), 2.36(s, 3H, CH ...

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Abstract

The invention discloses a synthesis method for multi-substituted 2-imidoimidazoline-4,5-diketone. The method comprises the following steps of: firstly reacting substituted carbodiimide and oxalyl chloride in an ether solvent; and then adding organic base of primary amine and non-primary amine to continuously react to produce the multi-substituted 2-imidoimidazoline-4,5-diketone. The method has is a universal method for synthesizing a multi-substitutent 2-imidoimidazoline-4,5-diketone derivative, has the advantages of high yield, readily available raw materials, easiness in operation, high separation yield and convenience in further development and application.

Description

technical field [0001] The invention relates to a general synthesis method of 2-iminoimidazoline-4,5-dione derivatives with various substituents, belonging to the field of organic synthesis. Background technique [0002] 2-iminoimidazoline-4,5-dione derivatives with various substituents are highly effective insecticides and herbicides in agricultural production, and are a class of highly efficient and environmentally friendly pesticide molecules. 2-iminoimidazoline-4,5-dione derivatives have a guanidinium moiety in their molecules, so they are widely used in medicine, have high biological activity, good antibacterial and anti-inflammatory activities, and It can be used as a thrombin inhibitor, angiotensin antagonist and various drug carriers, and the above applications make it an important medical lead compound. However, there are only sporadic reports on the synthesis methods of 2-iminoimidazoline-4,5-dione derivatives provided by literature at home and abroad, and the met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/96C07D417/12
Inventor 张文雄赵飞席振峰
Owner PEKING UNIV
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