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Ferrocenyl containing oxadiazolyl Mannich bases and preparation method thereof

A technology based on oxadiazolyl and amino oxadiazole is applied in the field of ferrocenyl-containing oxadiazolyl Mannich base and its preparation, and achieves the effects of high yield, mild reaction conditions and simple handling

Active Publication Date: 2017-03-08
SHAANXI UNIV OF SCI & TECH
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Problems solved by technology

The synthesis of ferrocene derivatives and oxadiazole derivatives has been reported, but there is no report on the introduction of oxadiazole in ferrocene derivatives. Therefore, to explore a synthetic ferrocene-containing oxadiazole Azolyl heterocyclic compounds have a certain significance

Method used

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  • Ferrocenyl containing oxadiazolyl Mannich bases and preparation method thereof
  • Ferrocenyl containing oxadiazolyl Mannich bases and preparation method thereof
  • Ferrocenyl containing oxadiazolyl Mannich bases and preparation method thereof

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preparation example Construction

[0032] The preparation method of aminooxadiazole containing substituents can refer to the literature: 2-amino-5-aryl-1,3,4-oxadiazole synthesis and process optimization, Liu Yuting, etc., "Journal of Shaanxi University of Science and Technology (Nature Science Edition), April 2015, Vol. 33, No. 2, pp. 79-82.

[0033] Concretely, the preparation method of aminooxadiazole containing substituent comprises the following steps:

[0034] 1) Add a mol semicarbazide hydrochloride and b mol absolute ethanol into a three-neck flask with a reflux condenser, and slowly add cmol aldehyde compounds dropwise, and reflux for 2 hours. After the reaction is completed, cool to room temperature, suction filter, and filter cake Dry to get hemiuret; wherein a:b:c=(0.9~1.2):(50~100):1; the structural formula of aldehydes is R 2 CHO;

[0035] 2) Add d mol hemiuret into a three-necked flask with a reflux condenser, and dropwise add e mol anhydrous sodium acetate dissolved in g mL glacial acetic acid...

Embodiment 1

[0037] Add 0.85mol 2-amino-5-(4-fluorophenyl)-1,3,4-oxadiazole to a dry three-necked flask with a reflux condenser, the mass percent concentration is 37% formaldehyde solution, 100mL of absolute ethanol as a solvent, during stirring, add 0.5mL of concentrated hydrochloric acid as a catalyst, then dropwise add a solution of acetylferrocene with a concentration of 0.5g / mL in absolute ethanol, heat and reflux at 80°C for 12h, pass through a TLC plate Monitor until complete reaction (developing solvent used by TLC is a mixture of dichloromethane and methanol with a volume ratio of 10:1). After the reaction, the reaction liquid was cooled, the solvent absolute ethanol was evaporated under reduced pressure, and then separated by silica gel column chromatography to obtain reddish-brown oily 3-(2-amino-5-p-fluorophenyl-1,3,4- Oxadiazole)-ethyl ferrocenyl ketone 126 mg, yield 63%. Wherein the formaldehyde solution contains 10mol of formaldehyde, and the absolute ethanol solution of ac...

Embodiment 2

[0040] Add 0.8mol 2-amino-5-(4-chlorophenyl)-1,3,4-oxadiazole to a dry three-necked flask with a reflux condenser, the mass percent concentration is 37% formaldehyde solution, 100mL of absolute ethanol as a solvent, during stirring, add 0.5mL of concentrated hydrochloric acid as a catalyst, then dropwise add a solution of acetylferrocene with a concentration of 0.5g / mL in absolute ethanol, heat and reflux at 80°C for 12h, pass through a TLC plate Monitor until complete reaction (developing solvent used by TLC is a mixture of dichloromethane and methanol with a volume ratio of 10:1). After the reaction, the reaction solution was cooled, the solvent absolute ethanol was evaporated under reduced pressure, and then separated by silica gel column chromatography to obtain reddish-brown oily 3-(2-amino-5-p-chlorophenyl-1,3,4- Oxadiazole)-ethyl ferrocenyl ketone, yield 65.7%. Wherein the formaldehyde solution contains 10mol of formaldehyde, and the absolute ethanol solution of acetyl...

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Abstract

The invention provides ferrocenyl containing oxadiazolyl Mannich bases and a preparation method thereof; the preparation method comprises: adding A mol of substituent-containing amino-oxadiazole, B mol of an aldehyde compound, an acidic catalyst and the solvent absolute ethyl alcohol into a dry three-neck flask with a reflux condensing tube, adding absolute ethyl alcohol solution of acetylferrocene with C mol of a solute, heating and refluxing until full reaction for 10-14 h, wherein the ratio of A, B and C is (0.7-1):(5-30):1, depressurizing and evaporating to remove the solvent after reaction, and separating via silica gel column chromatography to obtain the ferrocenyl containing oxadiazolyl Mannich bases. The preparation method is simple to perform, the reaction conditions are mild, equipment requirements are low, the purity of the bases is high, and the catalyst used herein is low in price and easy to obtain. The serial novel-structure ferrocenyl containing oxadiazolyl Mannich bases are prepared herein, and beneficial assistance is provided for the development and application of these compounds.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to a ferrocenyl-oxadiazolyl-containing Mannich base and a preparation method thereof. Background technique [0002] The structure of ferrocene is mainly that the iron atom is between two parallel cyclopentadiene, and the electron cloud density on the ring is relatively large, which promotes the electrophilic reaction. The special structure of ferrocene makes it in Optoelectronic materials have great prospects. Today, ferrocene derivatives have made great progress in medicine, optoelectronic materials and other aspects. Oxadiazole derivatives are also a class of compounds with certain antibacterial effects, and are widely used in the field of medicine. The synthesis of ferrocene derivatives and oxadiazole derivatives has been reported, but there is no report on the introduction of oxadiazole in ferrocene derivatives. Therefore, to explore a synthetic ferrocene-containin...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 刘玉婷辛宏尹大伟盛娇杨晓明乔倩瑜
Owner SHAANXI UNIV OF SCI & TECH
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