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A kind of synthetic method of 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxyl-4h,5h-1,2,4-oxadiazole compound

A technology of aminofurazan and synthesis method, applied in 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxy-4H,5H-1,2,4- The field of synthesis of oxadiazole compounds can solve the problems of low reaction yield and achieve the effect of high atom economy

Inactive Publication Date: 2016-05-25
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction yield of this method is low

Method used

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  • A kind of synthetic method of 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxyl-4h,5h-1,2,4-oxadiazole compound
  • A kind of synthetic method of 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxyl-4h,5h-1,2,4-oxadiazole compound
  • A kind of synthetic method of 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxyl-4h,5h-1,2,4-oxadiazole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 3-(3-aminofurazan-4-yl)-5,5-dimethyl-4-hydroxy-4H,5H-1,2,4-oxadiazole compound (Ⅰa)

[0020]

[0021] At a temperature of 20°C, add 0.477g (3mmol) of 3-amino-4-gemdioximofurazan and 6mL of ethanol into a round-bottomed flask with a suitable size magnet, stir and dissolve and add 0.87g (15mmol) ) acetone, and reacted for 2 hours at a temperature of 0° C. under stirring. After the reaction was completed, the ethanol was evaporated, and the resulting product was separated by column chromatography (the eluent was petroleum ether and ethyl acetate, and its volume ratio was 3:1) to obtain 3-(3-aminofurazan-4-yl)- 5,5-Dimethyl-4-hydroxy-4H,5H-1,2,4-oxadiazole, yield 98%.

[0022] Structure Identification:

[0023] Infrared Spectrum: IR(KBr,cm -1 )ν: 3467, 3339, 1636, 1604, 1523, 1375, 1103, 949, 800;

[0024] NMR: 1 HNMR (DMSO-d 6 ,500MHz), δ:9.81(s,1H,OH),6.33(s,2H,NH 2 ),1.49(s,6H,CH 3 );

[0025] 13 CNMR (DMSO-d 6 ,125MHz),δ:155.29,150.93,136.27...

Embodiment 2

[0031] Preparation of 3-(3-aminofurazan-4-yl)-5,5-dimethyl-4-hydroxy-4H,5H-1,2,4-oxadiazole compound (Ⅰa)

[0032]

[0033] At a temperature of 25°C, add 0.477g (3mmol) of 3-amino-4-gemdioximefuran and 3mL of tetrahydrofuran into a round-bottomed flask with a suitable size magnet, stir to dissolve and add 0.348g (6mmol) ) acetone, and reacted for 2 hours at a temperature of 20° C. under stirring. After the reaction was completed, tetrahydrofuran was distilled off, and the obtained product was separated by column chromatography (eluent was petroleum ether and ethyl acetate, the volume ratio was 3:1), and the target product Ia was obtained with a yield of 36%.

[0034] Structure Identification:

[0035] Infrared Spectrum: IR(KBr,cm -1 )ν: 3467, 3339, 1636, 1604, 1523, 1375, 1103, 949, 800;

[0036] NMR: 1 HNMR (DMSO-d 6 ,500MHz), δ:9.81(s,1H,OH),6.33(s,2H,NH 2 ),1.49(s,6H,CH 3 );

[0037] 13 CNMR (DMSO-d 6 ,125MHz),δ:155.29,150.93,136.27,102.82,21.78;

[0038] Elem...

Embodiment 3

[0043] Preparation of 3-(3-aminofurazan-4-yl)-5-methyl-5-ethyl-4-hydroxy-4H,5H-1,2,4-oxadiazole compound (Ⅰb)

[0044]

[0045] At a temperature of 25°C, add 0.477g (3mmol) of 3-amino-4-gemdioxime furazan and 6mL of isopropanol into a round-bottomed flask with a suitable size magnet, stir to dissolve and add 0.540g (7.5 mmol) methyl ethyl ketone, and reacted at a temperature of 40° C. under stirring for 3 hours. After the reaction is completed, the isopropanol is evaporated, and the resulting product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=3:1, volume ratio), and the target product 3-(3-aminofurazan-4- Base)-5-methyl-5-ethyl-4-hydroxyl-4H,5H-1,2,4-oxadiazole Ib, yield 72%.

[0046] The structural confirmation data of this product are as follows:

[0047] Infrared Spectrum: IR(KBr,cm -1 )ν: 3469, 3341, 1636, 1604, 1528, 1376, 1124, 958, 821;

[0048] NMR: 1 HNMR (DMSO-d 6 ,500MHz), δ:9.79(s,1H,OH),6.32(s,2H,NH 2 ),1.71-1.85(m,2H...

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Abstract

The invention discloses a synthetic method of a 3-(3-aminofurazan-4-yl)-5-methyl-5-substitute-4-hydroxy-4H,5H-1,2,4-oxadiazole compound. The method comprises the steps of adding 3-amino-4-geminal dioximidofurazan and an organic solvent to a reaction flask under stirring at a temperature ranging from 20 to 25 DEG C, next, adding an alkyl ketone, benzyl acetone or ethyl acetoacetate to the reaction flask, reacting for 15 minutes to 24 hours under stirring at a temperature ranging from 0 to 40 DEG C, removing the organic solvent by evaporating after the reaction is finished, and then subjecting the product to column chromatography isolation to obtain 3-(3-aminofurazan-4-yl)-5-methyl-5-substitute-4-hydroxy-4H,5H-1,2,4-oxadiazole, wherein the mol ratio of 3-amino-4-geminal dioximidofurazan to the ketone is 1: (1-5), the organic solvent is methanol, ethanol, isopropanol, tetrahydrofuran or acetonitrile, and the carbon number of the alkyl ketone is 3-7. The 3-(3-aminofurazan-4-yl)-5-methyl-5-substitute-4-hydroxy-4H,5H-1,2,4-oxadiazole compound synthesized by the synthetic method can be used for further synthesizing useful medical intermediates, and thus has potential medical value.

Description

technical field [0001] The invention relates to a synthesis method of 3-(3-aminofurazan-4-yl)-5-methyl-5-substituted-4-hydroxyl-4H,5H-1,2,4-oxadiazole compound. Background technique [0002] As an important structural structure of drug molecules, the oxadiazole functional group has obvious biological activity, and is usually used to replace unstable peptide bonds in drug molecules to achieve the purpose of resisting hydrolysis and improving activity. Among oxadiazole compounds, 1,2,4-oxadiazole derivatives have been widely used in medicinal chemistry. Studies have shown that after different substitutions at different positions of the oxadiazole ring, the antibacterial and antifungal activities of the drug will change greatly. In addition, 1,2,4-oxadiazole ring is rich in nitrogen and oxygen, and it is expected to be used in energetic materials after modification. [0003] At present, the research on compounds containing saturated 1,2,4-oxadiazole rings has been relatively ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/08
CPCC07D271/08
Inventor 刘宁翟连杰王伯周舒远杰张丽涵李辉李亚南霍欢贾思媛李祥志
Owner XIAN MODERN CHEM RES INST
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