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Imidazole-triazine type compound and preparation method and application thereof

A technology of s-triazine and imidazolium, applied to imidazo-s-triazine compounds and the fields of preparation and application thereof, can solve the problems of difficult control of reaction conditions, high toxicity, poor yield and the like, and achieves wide industrial application prospects , easy operation, low cost effect

Active Publication Date: 2017-08-25
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above method has the disadvantages of using highly toxic reagents, expensive catalysts or ligands, uneasy control of reaction conditions, cumbersome steps, and poor yields, and is subject to certain restrictions in the use process.

Method used

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  • Imidazole-triazine type compound and preparation method and application thereof
  • Imidazole-triazine type compound and preparation method and application thereof
  • Imidazole-triazine type compound and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0028] Example 1 Preparation of 2-amino-1,3,5-triazine compounds

[0029] Taking 2-amino-4-dimethylamino-1,3,5-triazine as an example, its preparation method is:

[0030] Mix metformin hydrochloride (1.6616g, 10.0323mmol), sodium methoxide (1.6200g, 29.9868mmol) in methanol (25mL), react at room temperature for 4h, add methyl formate (1.5011g , 24.9967mmol), continued the reaction at room temperature for 24h, evaporated the solvent under reduced pressure, added 10mL of water, filtered, and recrystallized the solid to obtain the target compound, 1.2826g, with a yield of 92%.

Embodiment 2

[0031] Example 2 Preparation of α, β-unsaturated ketones

[0032] Taking chalcone as an example, its preparation method is:

[0033] Benzaldehyde (1.1018g, 10.3822mmol) and acetophenone (1.2616g, 10.5001mmol) were dissolved in 30mL of ethanol, NaOH aqueous solution (0.8000g, 20.0016mmol dissolved in 30mL of water) was added dropwise at 0°C, and the addition was completed After that, it was stirred at room temperature for 3 hours, filtered, and the solid was recrystallized to obtain 1.7225 g of chalcone, with a yield of 82.7%.

[0034] The following Examples 3-17 were prepared according to the method described in Example 2, wherein different reaction substrates and their feeding amounts, different reaction products and their yields are listed in Table 1.

[0035] Reaction substrate and its charging amount in the embodiment 3~17 of table 1, reaction product and its productive rate

[0036]

[0037]

Embodiment 18

[0038] Embodiment 18: Preparation of compound III-1

[0039] 2-Amino-4-dimethylamino-1,3,5-triazine (0.1399g, 1.0053mmol), chalcone (0.1303g, 0.6257mmol) and chlorobenzene (2mL), iodine (0.3175g, 1.2509mmol) and copper chloride (0.0164g, 0.1220mmol) were added to the reactor, and reflux reaction (135°C) under oxygen conditions for 9h. Cool after the reaction, add 30 mL of 0.4M aqueous sodium thiosulfate solution to neutralize excess iodine, stir for 5 minutes, extract with ethyl acetate (20 mL × 3), combine the organic layers, concentrate, column chromatography (eluent is di Chloromethane:methanol=100:1, v:v), collect R f The eluate with a value of 0.1-0.55 (monitored by TLC, the developing solvent is the same as the eluent), the solvent was distilled off under reduced pressure, and dried to obtain 0.2023 g of the target compound (III-1), with a yield of 94%. 1 H NMR (500MHz, CDCl 3 ):δ=9.90(s,1H),7.47-7.46(m,2H),7.33-7.32(m,2H),7.29-7.25(m,1H),7.16-7.13(m,1H),7.11-7.08 (m...

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Abstract

The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.

Description

technical field [0001] The invention relates to a new class of imidazo-s-triazine compounds, their preparation method and application. Background technique [0002] The imidazo-s-triazine compounds have a variety of biological activities, such as folic acid antagonists, dihydrofolate reductase inhibitors and A1 adenosine receptor antagonists. At present, the synthesis methods of this type of compound mainly include the following types: 1. Preparation by reacting 2-aminoimidazole compound with N-acyl imidate, isothiocyanate or cyanamide as raw material. 2. Prepared by reacting 2-guanidinobenzimidazole with carbonyl-containing compounds such as diethyl azodicarboxylate, formaldehyde, acetone, orthoformate, etc. 3. Prepared by reacting s-triazine compounds with halogenated aldehydes and ketones. However, the above method has the disadvantages of using highly toxic reagents, expensive catalysts or ligands, uneasy control of reaction conditions, cumbersome steps, and poor yield...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/53A61P31/04
CPCC07D487/04Y02A50/30
Inventor 崔冬梅李进京张辰
Owner ZHEJIANG UNIV OF TECH
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