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Preparation method of 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound

A technology for oxadiazoles and compounds, which is applied in the field of preparation of 2-aryl-5--1,3,4-oxadiazoles, can solve complex synthesis methods, harsh reaction conditions, long reaction time, etc. The problem is that the synthesis method is simple, the reaction conditions are simple, and the reaction time is short.

Active Publication Date: 2019-06-14
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] (3) In 2007, Fung et al. reported a three-step reaction from 3-(4-Hydrazinocarbonyl-phenyl)sydnone to synthesize 4-(5-Aryl-1,3,4-oxadiazol-2-yl)phenyl-hydrazine method, although the reaction conditions are mild and carried out at room temperature, the reaction time is long, requiring 36 hours of reaction, and the reaction requires the use of explosive and highly corrosive perchloric acid, which has poor safety
[0025] To sum up, most of the methods reported in the literature currently adopt a multi-step synthesis strategy, the reaction conditions are harsh, the synthesis method is complicated, consumes a large amount of solvents and reagents, and pollutes the environment
Simultaneously, the starting material tribromotoluene, 2-(tribromomethyl)-quinoline, tetrazolium, acyl chloride etc. that above-mentioned method uses are not the raw material that commerce can buy, need to prepare through a series of steps, increased reaction time The cost also increases the pollution of the waste to the environment during the synthesis process

Method used

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  • Preparation method of 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound
  • Preparation method of 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound
  • Preparation method of 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation

[0047] The reaction formula is:

[0048]

[0049] The specific steps are: add 0.6mmol 2-methylquinoline, 0.9mmol elemental iodine, and 2mL dimethyl sulfoxide into a 15mL pressure tube, and stir the reaction at 110°C for 4 hours. After the reaction is cooled, add 0.5mmol Benzohydrazide and 3mmol potassium carbonate were magnetically stirred at 110°C for 6 hours. After the reaction was completed, the reaction solution was extracted, the organic layer was washed, dried, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was petroleum ether / Ethyl acetate = 10:1 (V / V) is the eluent, and the desired product is obtained by column separation and purification. The product is a yellow solid with a yield of 83%.

[0050] The result of the product identification data is: 1 H-NMR (400MHz, CDCl 3 ): δ (ppm) 8.40 (t, J = 8.4 Hz, 2H), 8.33 (s, 1H), 8.27-8.31 (m, 2H), 7.91 (dd, J = 1.2, 8.4 Hz, 1H), 7.67 ( dt, J = 1.2, 8...

Embodiment 2

[0051] Example 2: Preparation

[0052] The reaction formula is:

[0053]

[0054] The specific steps are: add 0.6mmol 2,6-dimethylquinoline, 0.9mmol elemental iodine, and 2mL dimethyl sulfoxide into a 15mL pressure tube, and magnetically stir the reaction at 110°C for 4 hours. After the reaction is cooled, Add 0.5mmol benzoyl hydrazide and 3mmol potassium carbonate, stir magnetically at 110°C for 6 hours. After the reaction is complete, extract the reaction solution, wash the organic layer, dry, and distill under reduced pressure to remove the solvent to obtain a crude product. Petroleum ether / ethyl acetate=10:1 (V / V) is the eluent, and the desired product is obtained by column separation and purification. The product is a yellow solid with a yield of 74%.

[0055] The result of the product identification data is: 1 H-NMR (400MHz, CDCl 3 ): δ(ppm) 8.31(d,J=8.4 Hz,1H),8.24-8.27(m,2H),8.21(d,J=8.4Hz,1H), 8.15(d,J=9.2Hz,1H) ,7.62(d, J=8.0Hz,2H),7.54-7.57(m,2H),7.53-7.54(m,1H),2.55(s,...

Embodiment 3

[0056] Example 3: Preparation

[0057] The reaction formula is:

[0058]

[0059] The specific steps are: add 0.6mmol 6-fluoro-2-methylquinoline, 0.9mmol elemental iodine, and 2mL dimethyl sulfoxide into a 15mL pressure tube, and magnetically stir the reaction for 4 hours at 110°C. After the reaction is cooled , Add 0.5mmol benzoyl hydrazide and 3mmol potassium carbonate, stir magnetically at 110°C for 6 hours. After the reaction is complete, extract the reaction solution, wash the organic layer, dry, and distill under reduced pressure to remove the solvent to obtain the crude product. Ethanol / dichloromethane was recrystallized and the product was a yellow solid with a yield of 70%.

[0060] The result of the product identification data is: 1 H-NMR (400MHz, CDCl 3 ): δ (ppm) 8.40 (d, J = 8.4 Hz, 1H), 8.30 (s, 1H), 8.29 (d, J = 8.0 Hz, 1H), 8.27 (t, J = 2.4 Hz, 1H), 8.25 (d,J=2.4Hz,1H),7.57-7.59(m,1H),7.57(t,J=2.4Hz,2H),7.55(d,J=1.6Hz,1H), 7.51(dd,J= 3.2,.8Hz,1H), 13 C-NMR (100MHz...

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Abstract

The invention discloses a preparation method of a 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound. The method comprises the following steps: enabling substituted methylquinoline and iodine simplesubstances to be in contact in advance; and after the methylquinoline disappears, adding aromatic ring or heteroaromatic ring substituted formylhydrazine under an alkaline condition, and continuing to react to obtain the 2-aryl-5-(2-quinolyl)-1,3,4-oxadiazole type compound. According to the preparation method disclosed by the invention, raw materials are cheap and are easy to obtain; the operation method is simple; reaction conditions are mild; the reaction can be performed by a one-pot method; the steps are short; the yield reaches up to 83 percent; and a feasible method is provided for preparing the type of compound in industry.

Description

Technical field [0001] The present invention relates to the field of organic synthesis, in particular to a preparation method of 2-aryl-5-(2-quinolinyl)-1,3,4-oxadiazole compounds. Background technique [0002] 2,5-Disubstituted-1,3,4-oxadiazole and its derivatives are an extremely important class of five-membered heterocyclic compounds. Because of its good anti-cancer, antihypertensive, anti-inflammatory, analgesic, antispasmodic, anti-edema, insecticidal and sterilization activities, it has been widely used in the fields of pesticides and medicine, such as the antihypertensive drug nesadil (Nesapidil) and the AIDS drug Raltegravir (Raltegravir) both contain 1,3,4-oxadiazole structural fragments. [0003] [0004] Roger et al. discovered a 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid compound, which has a regulatory effect on plant growth. [Roger L.N.Harris and John L.HuppatzAust.J. Chem.1977,30,2225-40] [0005] [0006] In addition, based on its optical and thermodynamic stabi...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D413/14
Inventor 祝艳平龙怡青胡江瑞刘兆亮翁卫钊吕旭成梁婧怡孟令瑜
Owner YANTAI UNIV
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