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Amide-substituted imidazo[1,3,5]triazine compounds, preparation method and application thereof
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A triazine compound and compound technology, which can be used in organic chemistry, resistance to vector-borne diseases, antibacterial drugs, etc., can solve problems such as few reports of biological activity in synthetic methods.
Active Publication Date: 2021-05-11
ZHEJIANG UNIV OF TECH
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[0004] Nitrogen heterocyclic compounds widely exist in natural products and have a variety of biological activities. Imidazotriazine compounds are an important class of compounds that have gradually attracted people's attention. There are few active reports, therefore, the preparation of novel imidazo[1,3,5]triazine compounds has important theoretical significance and practical application value
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Embodiment 1
[0024] 2-amino-4-dimethylamino-1,3,5-triazine (I-1) (139.2mg, 1.0mmol), 3-oxo-3-phenylpropanamide (II-1) ( 81.6mg, 0.5mmol), N-bromosuccinimide (93.4mg, 0.5mmol) were mixed in N-methylpyrrolidone (5mL), reacted at 80°C, followed by TLC monitoring, reacted for 7h, reacted After the end, add 30ml of water, extract with ethyl acetate (30mL×3), combine the organic layers, concentrate, column chromatography (eluent is petroleum ether:ethyl acetate=2:1, v:v), collect R f The eluent with a value of 0.3-0.35 (monitored by TLC, the developing solvent is the same as the eluent), the solvent was distilled off under reduced pressure, and dried to obtain 102.2 mg of the target compound (III-1), with a yield of 71%.
[0025] 1 H NMR (500MHz, CDCl 3 ):δ9.93(s,1H),7.75(s,2H),7.50(s,3H),5.73(s,1H),5.36(s,1H),3.35(s,3H),3.29(s, 3H).
[0026]
Embodiment 2
[0028] N-bromosuccinimide was changed to copper bromide (111.7mg, 0.5mmol), and other operations were the same as in Example 1. The yield was 101mg, and the yield was 70%.
Embodiment 3
[0030] N-methylpyrrolidone was changed to acetonitrile (2 mL), the temperature was changed to 50° C., other operations were the same as in Example 1, but the target product was not obtained.
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Abstract
The invention discloses an amido-substituted imidazo[1,3,5]triazine compound represented by formula (III), a preparation method and application thereof. The method is as follows: mix the triazine compound represented by the formula (I) and the β-ketoamide compound represented by the formula (II) into the solvent, and stir at a temperature of 50-120°C under the action of the halide After reacting for 5-20 hours, after the reaction is finished, the obtained reaction liquid is post-treated to prepare amido-substituted imidazo-s-triazine compounds represented by formula (III). The amido-substituted imidazo[1,3,5]triazine compound of the invention has a certain inhibitory effect on Escherichia coli, and has application prospects in the preparation of antibacterial drugs and antibacterial agents.
Description
[0001] (1) Technical field [0002] The invention relates to a new class of amido-substituted imidazol[1,3,5]triazine compounds, a preparation method and application thereof. [0003] (2) Background technology [0004] Nitrogen heterocyclic compounds widely exist in natural products and have a variety of biological activities. Imidazotriazine compounds are an important class of compounds that have gradually attracted people's attention. There are few active reports. Therefore, the preparation of novel imidazo[1,3,5]triazine compounds has important theoretical significance and practical application value. [0005] (3) Contents of the invention [0006] The present invention adopts following technical scheme: [0007] An amido-substituted imidazo[1,3,5]triazine compound as shown in formula (III): [0008] [0009] R in formula (III) 1 , R 2 Each is independently hydrogen, C1-C10 alkyl or C6-C10 aryl; preferably hydrogen, methyl, ethyl or phenyl. [0010] The present inve...
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