2-amido-5-substituted-1,3,4-oxadiazole as well as preparation method and application thereof

A technology of oxadiazole and amino, which is applied in the field of chemical synthesis, can solve problems such as side reactions, increased costs, and incomplete reactions, and achieve the effects of promoting reactions, simplifying post-treatment operations, and good antibacterial effects

Active Publication Date: 2014-08-13
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two methods are likely to cause incomplete reaction or the occurrence of side reactions; the third meth

Method used

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  • 2-amido-5-substituted-1,3,4-oxadiazole as well as preparation method and application thereof
  • 2-amido-5-substituted-1,3,4-oxadiazole as well as preparation method and application thereof
  • 2-amido-5-substituted-1,3,4-oxadiazole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Add Amol of 2-benzylidene semicarbazide, Bmol of manganese dioxide and CmL of pyridine to a dry three-necked flask, stir and react at 110°C, monitor the reaction with TLC during the reaction until the raw material point of semicarbazone Disappear, obtain reaction mixture; Wherein, A:B:C=1:1.2:10; The developer used during TLC monitoring is to be mixed with ethyl acetate and sherwood oil, and the volume ratio of ethyl acetate and sherwood oil 1:3;

[0034] 2) The reaction mixture was cooled to room temperature, filtered under reduced pressure, and the obtained filtrate was concentrated to dryness to obtain a white solid, which was washed with water and filtered under reduced pressure to obtain a crude product, which was recrystallized with absolute ethanol to obtain 2 -Amino-5-phenyl-1,3,4-oxadiazole pure product, the yield can reach more than 93%.

[0035] m.p.=153~154℃; IR(KBr, ν / cm -1 ): 3396.24, 3301.59, 1655.72, 1325.30, 1124.73.

Embodiment 2

[0037] 1) Add Amol of 2-(2'-chlorophenyl)methylene semicarbazide, Bmol of manganese dioxide and CmL of pyridine to a dry three-necked flask, stir and react at 110°C, monitor the reaction with TLC during the reaction Until the raw material point of semicarbazone disappears, a reaction mixture is obtained; wherein, A:B:C=1:1.2:10; the developing agent used during TLC monitoring is formed by mixing ethyl acetate and sherwood oil, and ethyl acetate The volume ratio of ester and petroleum ether is 1:3;

[0038]2) The reaction mixture was cooled to room temperature, filtered under reduced pressure, and the obtained filtrate was concentrated to dryness to obtain a white solid, which was washed with water and filtered under reduced pressure to obtain a crude product, which was recrystallized with absolute ethanol to obtain 2 -Amino-5-(2'-chlorophenyl)-1,3,4-oxadiazole pure product, the yield can reach more than 93%.

[0039] The determination data of 2-amino-5-(2'-chlorophenyl)-1,3,4...

Embodiment 3

[0043] 1) Add Amol of 2-(2'-hydroxyphenyl)methylene semicarbazide, Bmol of manganese dioxide and CmL of pyridine to a dry three-necked flask, stir and react at 100°C, monitor the reaction with TLC during the reaction Until the raw material point of semicarbazone disappears, a reaction mixture is obtained; wherein, A:B:C=1:1:12; the developing agent used during TLC monitoring is formed by mixing ethyl acetate and sherwood oil, and ethyl acetate The volume ratio of ester and petroleum ether is 1:3;

[0044] 2) The reaction mixture was cooled to room temperature, filtered under reduced pressure, and the obtained filtrate was concentrated to dryness to obtain a white solid, which was washed with water and filtered under reduced pressure to obtain a crude product, which was recrystallized with absolute ethanol to obtain 2 -Amino-5-(2'-hydroxyphenyl)-1,3,4-oxadiazole pure.

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Abstract

The invention relates to 2-amido-5-substituted-1,3,4-oxadiazole as well as a preparation method and application thereof. The preparation method comprises the following steps: adding semicarbazone, manganese dioxide and pyridine into a reaction vessel, reacting at 100-120 DEG C, and monitoring the reaction by using TLC (Thin Layer Chromatography) till the raw material point of the semicarbazone disappears in a reaction process to obtain a reaction mixture; cooling the reaction mixture to room temperature, concentrating filter liquor obtained through decompressed suction filtration to be dry to obtain a solid, carrying out washing and the decompressed suction filtration on the solid to obtain a crude product, and recrystallizing the crude product to obtain the 2-amido-5-substituted-1,3,4-oxadiazole. The compound disclosed by the invention can be applied as a gram-negative bacteria resistant medicament or applied to a fluorescent material. The preparation method disclosed by the invention has the advantages of easiness and convenience for operation, higher productivity, recycling and reutilization of a catalyst, safety and environmental friendliness, meets the requirement for industrial production and is an economical, simple, convenient and environment-friendly synthetic method.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a 2-amino-5-substituted-1,3,4-oxadiazole and its preparation method and application. Background technique [0002] 1,3,4-Oxadiazoles have a wide range of biological activities, such as anti-inflammatory, antibacterial, insecticidal, plant growth promotion and sedative CNS. In addition, 1,3,4-oxadiazole compounds have good heat resistance, oxidation resistance and certain electron accepting ability. In electroluminescence devices, the 1,3,4- The oxadiazole ring is also a good electron acceptor. Introducing it into the hole transport material can enhance the ability to accept electrons, so that electrons can easily enter the carrier transport layer and recombine with holes to emit light to produce strong electroluminescence. . [0003] At present, the synthesis of oxadiazole ring generally can adopt 3 kinds of methods: one is by hydrazide and carboxylic acid directly under the a...

Claims

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Application Information

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IPC IPC(8): C07D271/113A61K31/4245A61P31/04C09K11/06H01L51/54
CPCC09K11/06C07D271/113C09K2211/1048H10K85/6565
Inventor 尹大伟张晓莉刘玉婷乔森赵斌杰杨阿宁王金玉吕博
Owner SHAANXI UNIV OF SCI & TECH
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