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Method for preparing ferrocenyl oxadiazole-based Mannich alkali

A technology based on oxadiazolyl and ferrocene, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of high reaction temperature, long reaction time, and many by-products, etc., and achieves low reaction temperature, The effect of short reaction time and less environmental pollution

Active Publication Date: 2017-09-29
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing method for preparing heterocyclic compounds containing ferrocenyl oxadiazolyl has longer reaction time, higher reaction temperature, more by-products and low yield

Method used

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  • Method for preparing ferrocenyl oxadiazole-based Mannich alkali
  • Method for preparing ferrocenyl oxadiazole-based Mannich alkali
  • Method for preparing ferrocenyl oxadiazole-based Mannich alkali

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 0.8mmol of 2-amino-5-(4-methylphenyl)-1,3,4-oxadiazole and 45mmol of formaldehyde to a dry three-necked flask with a reflux condenser at a volume concentration of 37%. Formaldehyde solution, and add 20mL of absolute ethanol as a solvent, add 1.2mmol bismuth nitrate pentahydrate as a catalyst during the stirring process, and use a constant pressure titration funnel to dropwise add acetyl The dehydrated ethanol solution of base ferrocene was reacted at room temperature for 3h, and the reaction process was monitored by TLC plate (when the raw material point of 2-amino-5-(4-methylphenyl)-1,3,4-oxadiazole When it disappears, it means that the reaction is complete. The developer used in the TLC plate is a mixed solution of dichloromethane and methanol with a volume ratio of 10:1). Separation (a mixture of petroleum ether and ethyl acetate with a volume ratio of 3:1 is the first eluent to wash off unreacted acetyl ferrocene, and a mixture of petroleum ether and ethyl aceta...

Embodiment 2

[0034]Add 0.75 mmol of 2-amino-5-(4-methoxyphenyl)-1,3,4-oxadiazole and 45 mmol of formaldehyde to a dry three-necked flask with a reflux condenser to a volume concentration of 37 % formaldehyde solution, and add 20mL of absolute ethanol as a solvent, add 1.2mmol bismuth nitrate pentahydrate as a catalyst during the stirring process, and use a constant pressure titration funnel to add dropwise The dehydrated ethanol solution of acetylferrocene was reacted at room temperature for 5h, and the reaction progress was monitored by a TLC plate (when 2-amino-5-(4-methoxyphenyl)-1,3,4-oxadiazole When the raw material point disappears, it means that the reaction is complete. The developing agent used in the TLC plate is a mixed solution of dichloromethane and methanol with a volume ratio of 10:1). Column chromatographic separation (with a volume ratio of 3:1 the mixed solution of petroleum ether and ethyl acetate as the first eluent to wash off unreacted acetyl ferrocene, with a volume ...

Embodiment 3

[0037] Add 0.7mmol of 2-amino-5-(4-bromophenyl)-1,3,4-oxadiazole and 37% oxadiazole containing 45mmol formaldehyde to a dry three-necked flask with a reflux condenser. Formaldehyde solution, and add 20mL of absolute ethanol as a solvent, add 1.1mmol bismuth nitrate pentahydrate as a catalyst during the stirring process, and use a constant pressure titration funnel to dropwise add acetyl ferrocene containing 1mmol with a concentration of 0.4g / mL The dehydrated ethanol solution of ferrocene was reacted at room temperature for 6h, and the reaction process was monitored by TLC plate (when the raw material point of 2-amino-5-(4-bromophenyl)-1,3,4-oxadiazole disappeared Indicates that the reaction is complete, the TLC plate used developing agent is a mixed solution of dichloromethane and methanol in a volume ratio of 10:1), after the reaction, the solvent absolute ethanol is evaporated by rotary evaporation under reduced pressure, and then separated by column chromatography ( The mi...

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Abstract

The invention provides a method for preparing ferrocenyl oxadiazole-based Mannich alkali. The method comprises the following steps: putting A mol 2-amino-5-substituted 1,3,4-oxadiazole, B mol substituted aldehyde, an E mol catalyst and a solvent, namely absolute ethyl alcohol into a dry three-mouth flask with a backflow condensation tube, putting an absolute ethyl alcohol solution of C mol acetyl ferrocene, performing reaction at room temperature for 3-6 hours, wherein the ratio of A to B to C to E is (0.7-1):(1-45):1:(1.1-1.5), after the reaction is completed, performing vacuum distillation on a reaction mixed liquid so as to remove the solvent, and treating with column chromatography, thereby obtaining the ferrocenyl oxadiazole-based Mannich alkali. The method is simple to operate, gentle in reaction condition, low in equipment requirement and high in product purity, and the catalyst is bismuth nitrate which is cheap and easy to obtain.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing a ferrocenyl oxadiazolyl Mannich base. Background technique [0002] Ferrocene is an important metallocene-based complex. Due to its stability, aromaticity, low toxicity and redox properties, it has a wide range of applications and can be used in industry, medicine, materials and optoelectronics. Oxadiazole derivatives are also a class of compounds with certain antibacterial effects, and are widely used in the field of medicine. [0003] The existing methods for preparing heterocyclic compounds containing ferrocenyl oxadiazolyl groups have long reaction time, high reaction temperature, many by-products and low yield. Therefore, it is of certain significance to explore a method for synthesizing ferrocenyl-oxadiazolyl-containing heterocyclic compounds with simple reaction conditions and high yield. [0004] Mannich bases have certain applications in the fi...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 刘玉婷辛宏尹大伟赵博航杨紫江盛娇杨晓明倪艺萌
Owner SHAANXI UNIV OF SCI & TECH
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