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Preparation method of 2-amino-1, 3, 4-oxadiazole compound and prepared compound

A technology of oxadiazoles and compounds, applied in the field of medicinal chemistry, can solve problems such as harsh conditions, expensive catalysts, unfavorable industrial production, etc.

Active Publication Date: 2021-08-27
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(3) Cyclization of amino acid-derived thiosemicarbazides mediated by EDCl or TBTU to obtain 2-amino-1,3,4-oxadiazoles, but EDCI is expensive and the reaction needs to be carried out at 60 degrees Celsius
IBX is an expensive oxidizing agent, which is expensive, and the reaction needs to be carried out under more severe microwave conditions
(5) I 2 A synthetic approach mediated by C-O / C-S oxidative bond formation yields 2-amino-1,3,4-oxadiazoles, but iodine is corrosive and prone to sublimation
In summary, most of the reported 2-amino-1,3,4-oxadiazole synthesis methods have disadvantages such as long reaction time, harsh conditions, and expensive catalysts, which are not conducive to industrial production.

Method used

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  • Preparation method of 2-amino-1, 3, 4-oxadiazole compound and prepared compound
  • Preparation method of 2-amino-1, 3, 4-oxadiazole compound and prepared compound
  • Preparation method of 2-amino-1, 3, 4-oxadiazole compound and prepared compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 N, the preparation of 5-diphenyl-1,3,4-oxadiazol-2-amine

[0030]Add benzohydrazide (0.20 g, 1.46 mmol), phenylisothiocyanate (0.20 g, 1.5 mmol), dimethyl sulfoxide (DMSO) 3 mL into a 50 mL eggplant-shaped flask, stir at room temperature for 30 min, add KHSO 4 (1.19 g, 8.75 mmol), the reaction was continued at room temperature for 6 h. After the reaction was completed, 30 ml of water was added, filtered, and the solid was dried and purified by column chromatography to obtain 0.29 g of a light red solid with a yield of 84%. m.p.207-209°C; 1 H NMR (600 MHz, DMSO-d 6 )(δ,ppm):10.68(s,1H),7.98–7.82(m,2H),7.69–7.50(m,5H), 7.37(dd,J=8.2,7.6Hz,2H),7.02(t, J=7.3Hz,1H); 13 CNMR (150MHz, DMSO-d 6 )(δ,ppm):160.38,158.19,139.10,131.44,129.82,129.57,126.00,124.33, 122.36,117.53. HRMS(ESI):m / z[M+Na]+Calcd for C14H11N3O:237.0902; .

Embodiment 2

[0031] Example 2 N, the preparation of 5-diphenyl-1,3,4-oxadiazol-2-amine

[0032] Add benzohydrazide (0.20 g, 1.46 mmol), phenylisothiocyanate (0.20 g, 1.5 mmol), dimethyl sulfoxide (DMSO) 3 mL into a 50 mL eggplant-shaped flask, stir at room temperature for 30 min, add KHSO 4 (1.79 g, 13.14 mmol), the reaction was continued at room temperature for 2 h. After the reaction was completed, 30 ml of water was added, filtered, and the solid was dried and purified by column chromatography to obtain 0.22 g of a light red solid with a yield of 63%.

Embodiment 3

[0033] Example 3 N, the preparation of 5-diphenyl-1,3,4-oxadiazol-2-amine

[0034] Add benzohydrazide (0.20 g, 1.46 mmol), phenylisothiocyanate (0.20 g, 1.5 mmol), dimethyl sulfoxide (DMSO) 3 mL into a 50 mL eggplant-shaped flask, stir at room temperature for 30 min, add KHSO 4 (0.59 g, 4.38 mmol), the reaction was continued at room temperature for 12 h. After the reaction was completed, 30 ml of water was added, filtered, and the solid was dried and purified by column chromatography to obtain 0.24 g of a light red solid with a yield of 70%.

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Abstract

The invention belongs to the field of medical chemistry, and particularly relates to a preparation method of a 2-amino-1, 3, 4-oxadiazole compound and the compound prepared by the preparation method. According to the method, the 1, 3, 4-oxadiazole compound is prepared by taking the isothiocyanate compound and the benzoyl hydrazine compound as raw materials and taking the mild, cheap and easily available potassium hydrogen sulfate as the catalyst, so that not only is the use of harmful reagents with relatively strong corrosivity such as sulfuric acid avoided, but also the yield can be up to 85%, and the method is convenient in post-treatment and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 2-amino-1,3,4-oxadiazole compounds and the prepared compound. Background technique [0002] 2-Amino-1,3,4-oxadiazoles are an important class of heterocyclic compounds with a wide range of biological activities, such as muscle relaxation, anticancer, antibacterial, antiproliferative, antiinflammatory and antimitotic, etc. Anti-inflammatory and anti-infective compounds shown in formula a, antibiotic furamizole (Furamizole) shown in formula b, antibacterial and antifungal compounds shown in formula c, all contain 2-amino-1,3,4 in their structures - The key skeleton of oxadiazole. [0003] [0004] At present, there are several methods for synthesizing 1,3,4-oxadiazoles: (1) using sulfur powder to promote the cyclization of p-toluylhydrazide and cyclohexylisonitrile to synthesize 2-amino-1,3 ,4-Oxadiazole. The reaction uses sulfur powder wh...

Claims

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Application Information

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IPC IPC(8): C07D271/113C07D413/04
CPCC07D271/113C07D413/04
Inventor 甘宗捷余瑜隆冰羽田冰化
Owner CHONGQING MEDICAL UNIVERSITY
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