138723-98-5

Usage

Structure

Oxadiazole derivative with a phenyl group and a propyl chain

Applications

a. Organic synthesis
b. Medicinal chemistry
c. Building block for pharmaceuticals and bioactive molecules

Biological activities

a. Antimicrobial
b. Anticancer
c. Anti-inflammatory

Potential uses

a. Therapeutic agent
b. Corrosion inhibitor
c. Component in materials science for polymer and nanocomposite development

Upstream product

• 17531-54-3 butyric acid benzylidenehydrazide 
• 99840-61-6 N'-(n-butylidene)benzohydrazide 
• 613-94-5 benzoic acid hydrazide 
• 100-47-0 benzonitrile 
• 71-36-3 butan-1-ol 
• 3538-65-6 butyric acid hydrazide 
• 611-74-5 N,N-dimethylbenzamide 
• 14389-13-0 5‐propyl‐1H‐1,2,3,4‐tetrazole 
• 3282-30-2 pivaloyl chloride 
• 611-73-4 Benzoylformic acid 
• 93-58-3 benzoic acid methyl ester 
• 123-72-8 butyraldehyde 
• 107-92-6 butyric acid 
• 24964-76-9 triethyl orthobutyrate 

Relevant academic research and scientific papers

A mild method for the preparation of 1,3,4-oxadiazoles: Triflic anhydride promoted cyclization of diacylhydrazines

Diacylhydrazines undergo cyclization upon treatment with triflic anhydride and pyridine to form the corresponding 1,3,4-oxadiazoles in yields ranging from 70-95%.

TiCl4 mediated facile synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles

An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles has been developed. Various hydrazides or thionyl hydrazides readily react with DMA derivatives in the presence of TiCl4 as a catalyst to afford the desired products. This protocol provides a simple and economical procedure that affords the target products with good yields and wide substrate scope.

Batch Versus Flow Lithiation–Substitution of 1,3,4-Oxadiazoles: Exploitation of Unstable Intermediates Using Flow Chemistry

1,3,4-Oxadiazoles are a common motif in pharmaceutical chemistry, but few convenient methods for their modification exist. A fast, convenient, high yielding and general α-substitution of 1,3,4-oxadiazoles has been developed using a metalation-electrophilic trapping protocol both in batch and under continuous flow conditions in contradiction to previous reports which suggest that α-metalation of this ring system results in ring fragmentation. In batch, lithiation is accomplished at an industrially convenient temperature, ?30 °C, with subsequent trapping giving isolated yields of up to 91 %. Under continuous flow conditions, metalation is carried out at room temperature, and subsequent in flow electrophilic trapping gave up to quantitative isolated yields. Notably, lithiation in batch at room temperature results only in ring fragmentation and we propose that the superior mixing in flow allows interception and exploitation of an unstable intermediate before decomposition can occur.

Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones

A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction mechanism was proposed.

Alkyl aryl-substituted oxadiazole compound of three-component synthetic method (by machine translation)

The invention relates to a kind of the following formula (III) alkyl aryl substituted oxadiazoles as shown in synthetic method of compound, said method comprising: in the organic solvent, the following formula (I) compounds, of formula (II) compound and amine source compound, the catalyst, alkali, additive and the presence of oxidation aid, for 80 - 100 °C lower reaction 6 - 10 hours, the reaction is finished after treatment, thereby obtaining states the type (III) compound, Wherein R1 For C1 - C6 Alkyl; R2 Is H, C1 - C6 Alkyl, C1 - C6 Alkoxy or halogen. The method by adopting specific three-component reaction system, and the particular oxidation agent, the addition of specific catalytic system integrated synergistic, thus can yield to obtain the target product, has good application prospect and value. (by machine translation)

Three-component synthesis method of oxadiazole compound

The invention relates to a synthesis method of an oxadiazole compound shown in formula (III). The method comprises steps as follows: a compound shown in formula (1), a compound shown in formula (II) and an amine source compound react at 80-100 DEG C for 6-10 h in the presence of an organic solvent, a catalyst, base and an additive, after-treatment is performed after the reaction ends, and the compound shown in formula (III) is obtained, wherein R1 is C1-C6 alkyl groups, phenyl groups or phenyl groups substituted with substitute groups, substitute groups are C1-C6 alkyl groups, C1-C6 alkoxy groups or halogen, and R2 is H, C1-C6 alkyl groups, C1-C6 alkoxy groups or halogen. A specific three-component reaction system is adopted in the method, comprehensive synergism of a specific catalytic system is combined, so that a target product can be obtained at the high yield, and the method has good application prospect and value.

A process for preparing 2, 5 - disubstituted - 1, 3, 4 - oxadiazoles (by machine translation)

The invention provides a method for catalytic oxidative cyclization of formula (II) is shown in the 1, 3, 4 - oxadiazole method, said method comprising: in order to having a structure of formula (I) indicated by the formyl zong compound as a raw material, in order to air or oxygen atmosphere, in order to nitric acid the iron is catalyst, in order to 2, 2, 6, 6 - tetramethyl piperidine nitrogen oxides as initiator, under the action of the water absorbing agent, under the action of the water absorbing agent, in an organic solvent, for 25 - 60 °C lower reaction 3 - 12h, and the resulting reaction solution by the following formula (II) after treatment indicated by the 1, 3, 4 - oxadiazole compounds; the reaction of the invention speed, mild condition, easy operation, low cost, safe reaction, the whole process is friendly to the environment, pollution-free. (by machine translation)

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O 2.

Iodine-catalysed oxidative cyclisation of acylhydrazones to 2,5-substituted 1,3,4-oxadiazoles

An environmentally benign synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed starting from N-aroylhydrazones and N-acetylhydrazones at room or ambient temperature using a catalytic quantity of iodine in the presence of an aqueous hydrogen peroxide oxidant.

I2-mediated oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides

A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A series of symmetrical and asymmetrical 2,5-disubstituted (aryl, alkyl, and/or vinyl) 1,3,4-oxadiazoles can be conveniently generated in an efficient and scalable fashion.