59663-63-7

Usage

Heterocyclic aromatic compound

It has a ring structure containing both carbon and hetero atoms (nitrogen and oxygen), which gives it aromatic properties.

Contains nitrogen and oxygen atoms

The presence of nitrogen and oxygen atoms in its structure contributes to its unique chemical properties and potential applications.

Potential applications in organic synthesis

The compound may be used as an intermediate or building block in the synthesis of other organic compounds.

Potential applications in medicinal chemistry

Due to its unique structural features, it may be useful in the development of pharmaceutical drugs.

Possible use in materials science

The compound's properties may make it suitable for use in the development of new materials or coatings.

Potential use as a fluorescent dye in biological research

The compound may exhibit fluorescent properties, making it useful as a dye or marker in biological research.

Need for further research and experimentation

The specific uses and properties of 2-(2-methylphenyl)-5-phenyl-1,3,4-oxadiazole would need to be determined through laboratory testing and experimentation.

Upstream product

• 65349-16-8 N'-(2-methyl-benzoyl)-benzohydrazonic acid amide 
• 7658-80-2 2-methylbenzohydrazide 
• 100-52-7 benzaldehyde 
• 65349-09-9 N-benzoyl-N'-2-methylbenzoylhydrazide 
• 65349-27-1 (E)-N'-benzylidene-2-methylbenzohydrazide 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 607-86-3 2-methylbenzoic anhydride 
• 118-90-1 ortho-methylbenzoic acid 
• 613-94-5 benzoic acid hydrazide 
• 51449-86-6 5-(2-methylphenyl)-2H-tetrazole 
• 529-20-4 2-methylphenyl aldehyde 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 591-50-4 iodobenzene 
• 119072-55-8 tert-butylisonitrile 

Downstream Products

• 56894-37-2 2-(5-phenyl-1,3,4-oxadiazole-2-yl)-benzoic acid 

Relevant academic research and scientific papers

Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow

A range of 1,3,4-oxadiazoles have been synthesized using a UV-B activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.

Photocatalyzed facile synthesis of 2,5-diaryl 1,3,4-oxadiazoles with polyaniline-?g-C3N4-TiO2 composite under visible light

PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for the synthesis of 2,5-diaryl 1,3,4-oxadiazoles under visible light. This reaction involved decarboxylation and cyclization from α-keto acids with acylhydrazines, and a broad scope of substrates were tolerated to provide the desired products in moderate to good yields. Control experiments indicated that a radical pathway was involved in the present photocatalytic reaction and a synergistic effect may exist in the ternary composite. Moreover, this semiconductor photocatalyst could be readily recovered and showed good reusability with only slight decrease in the catalytic activity after six consecutive runs.

One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions

A one-pot KI/TBHP-mediated oxidative cyclization of α-keto acids with acylhydrazines was developed. A series of functional 2,5-disubstituted 1,3,4-oxadiazoles were synthesized through a tandem keto amine condensation followed by oxidative cyclization and decarboxylation reactions. This procedure was achieved under transition-metal-free conditions and showed advantages including readily available materials, mild reaction conditions and good group tolerance.

Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source

A palladium-catalyzed aminocarbonylation reaction of aryl halides with chloroform and tetrazoles has been developed, where chloroform was employed as the carbon monoxide (CO) source in the presence of cesium hydroxide. The in situ generated N-acylated tetrazoles were unstable and easily decomposed to afford 2,5-disubstituted 1,3,4-oxadiazoles. A wide range of tetrazoles and aryl halides reacted smoothly under the optimized reaction conditions to give the corresponding products in moderate to good yields.

Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion

An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs diazoles in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.

Organocatalytic Oxidative Amidation of Aldehydes with Tetrazoles to Construct 2,5-Diaryl 1,3,4-Oxadiazoles

A practical and metal-free oxidative amidation of aldehydes with tetrazoles into 1,3,4-oxadiazoles has been developed by employing tetrabutylammonium iodide (TBAI) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant. A wide range of 2,5-disubstituted 1,3,4-oxadiazoles can be conveniently generated in moderate to good yields. Gram-scale reaction was also realized in this catalytic system..

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields. (Chemical Equation Presented).

Efficient oxidative cyclization of N -acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions

An efficient procedure for the oxidative cyclization of N -acylhydrazones was developed utilizing tert-butyl hypoiodite (t-BuOI), which is generated in situ from t -BuOCl and NaI. A variety of 2,5-disubstituted 1,3,4-oxadiazoles were synthesized in high yields within short reaction time. The method is also suitable for cyclization of N -acylhydrazones derived from heterocyclic aldehydes and aliphatic aldehydes. Mild reaction conditions and simple workup operations make the procedure a good alternative for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles.

Mild and convenient one-pot synthesis of 1,3,4-oxadiazoles

A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted- 1,3,4-oxadiazoles in good to very good yields.