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Functionalized united imidazole derivative and synthesizing method thereof

A technology of functional grouping and synthesis method, applied in the direction of organic chemistry, etc., to achieve the effect of simple and economical operation, easy post-processing, and mild reaction conditions

Inactive Publication Date: 2012-10-10
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are relatively few biimidazole derivatives and related preparation methods. The present invention relates to biimidazole derivatives and a preparation method thereof

Method used

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  • Functionalized united imidazole derivative and synthesizing method thereof
  • Functionalized united imidazole derivative and synthesizing method thereof
  • Functionalized united imidazole derivative and synthesizing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of 1,1'-bis(amidomethyl)-2,2'-biimidazole

[0053] Add 5g (0.125mol) of solid sodium hydroxide to 13.4g (0.1mol) of 2,2′-biimidazole in DMF (100mL) suspension, and heat to 80°C under stirring. After stirring for 30 minutes, the solution turns dark green , dropwise added a DMF solution of 2-chloroacetamide (0.1mol), the concentration was 0.2mol / 100mL, and the dropwise addition was completed in 15 minutes. After 30 minutes of reaction, 4 g (0.1mol) of sodium hydroxide solid was added, and after another 30 minutes, dropwise Add the same part of the DMF solution of 2-chloroacetamide, the concentration is 0.2mol / 100mL, after the dropwise addition, the reaction is kept at 80°C for 6 hours. Naturally cooled to room temperature, a light yellow solid precipitated, which was recrystallized twice with ethanol to obtain a white solid product.

[0054] Infrared: (KBr, cm -1 ): 3363, 1658, 1334, 1101, 686. The infrared spectrum of the product is attached figure 1 .

Embodiment 2

[0056] Preparation of 1,1'-bis(2-amidoethyl)-2,2'-biimidazole

[0057] 2,2'-Bimidazole 13.4g (0.1mol) in DMF (100mL) suspension, add 0.8g (0.02mol) sodium hydroxide 10mL aqueous solution, and heat to 100°C while stirring. Add a solution of 14.2g (0.2mol) of acrylamide in DMF (50mL) dropwise, the concentration is 0.4mol / 100mL, biimidazole is slowly dissolved to obtain a clear solution, the color of the solution is from colorless, green to orange. After refluxing for six hours, cool naturally, distill DMF under reduced pressure to the remaining 1 / 4 volume, and solid precipitates, then put it in the refrigerator to freeze for 10 hours, filter while cold, wash with 10mL ether for 3 times, and dry in vacuum to obtain a white solid 20.57 g, Yield: 74.3%.

[0058] IR: (KBr, cm -1 ): 3388, 1674, 1409, 1267, 769; 1 H NMR: (400MHz, D 2 O, 25°C, TMS, ppm) δ: 8.402 (s, 4H), 7.306 (s, 2H), 7.140 (s, 2H), 4.374 (s, 4H), 2.627 (s, 4H). 13 C NMR: (100MHZ, D 2 O, 25°C, TMS, ppm) δ: 171.5...

Embodiment 3

[0061] Preparation of 1,1'-bis(carboxymethyl)-2,2'-biimidazole

[0062] Take 1.28g (6.04mmol) of 1,1'-bis(cyanomethyl)-2,2'-biimidazole and add it to 3mL (54mmol) of 98% concentrated sulfuric acid in water, heat to 100°C, and reflux for 10 hours , after cooling, the pH was adjusted to 1 with 1M aqueous sodium hydroxide solution, and a solid precipitated out, filtered, washed twice with a small amount of water, and dried in vacuo to obtain 0.862 g of a white solid product, yield: 62%.

[0063] IR: (KBr, cm -1 ): 3145, 1732, 1348, 1245, 767. 1 H NMR: (400MHz, D 2 O, 25°C, TMS, ppm) δ: 12.921 (s, 2H), 7.280 (d, J = 0.8 Hz, 2H), 6.997 (d, J = 0.8 Hz, 2H), 5.309 (s, 4H). 13 C NMR: (100MHz, D 2 O, 25°C, TMS, ppm) δ: 169.78, 137.84, 127.02, 123.41, 49.00.

[0064] The infrared spectrum, proton nuclear magnetic resonance spectrum and carbon spectrum of the product are shown in the appendix Figure 5 , 6, 7.

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Abstract

The invention relates to a functionalized united imidazole derivative and a synthesizing method thereof. More particularly, the functionalized united imidazole derivative is a derivative of 1, 1-dsubstituted united imidazole acidamide, united imidazole carboxylic acid or united imidazole amine shown by formula I, wherein n is equal to 1 or 2; and X is acylamino, carboxyl or amido. A method for preparing the united imidazole acidamide comprises: taking united imidazole as raw material and N, N-dimethyl formamide as solvent; and leading the united imidazole and the N, N-dimethyl formamide to have Michael addition or nucleophilic substitution reaction together with acrylamide and chloroacetamide under the alkali condition, and obtaining the united imidazole acidamide; a method for preparing the united imidazole carboxylic acid comprises: taking united imidazole nitriles derivative as raw material, and having hydrolysis reaction under the acidic condition to obtain the united imidazole carboxylic acid; a method for preparing the united imidazole amine comprises: taking the united imidazole acidamide as raw material, and carrying out Hofmann degradation to obtain the united imidazole amine; and the united imidazole derivative also can be further modified by alkylation, and the functionalized ionic liquid material can be obtained by carrying out quaternization on imine of imidazole ring. As activated side chain radical is introduced, further derivatization can be carried out.

Description

technical field [0001] The present invention relates to functionalized biimidazole derivatives such as biimidazole amide derivatives, biimidazole carboxylic acid, biimidazole amine derivatives and related synthesis methods. Background technique [0002] As an important aromatic heterocyclic compound, imidazole exists widely in nature. Important physiologically active substances such as: amino acids, nucleic acids, proteins, etc. all have imidazole components. Due to the characteristics of its chemical structure, imidazole-containing compounds are widely used, and have important application values ​​in the fields of medicine, pesticides, functional materials, and devices. For example: in medicine, it can be used as a preventive and therapeutic agent for respiratory diseases, vascular diseases, peripheral circulatory disorders, nervous disorders, cognitive impairment, tissue damage, ulcers, fungicides in pesticides, metal surface preservatives, functional ionic liquids, Elec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/56C07D233/61
Inventor 梁洪泽任英涛张涛张婷婷李月娇
Owner NINGBO UNIV
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