52596-95-9

Usage

Chemical structure

A heterocyclic organic compound with a five-membered ring containing oxygen, nitrogen, and two carbon atoms.

Molecular weight

269.7 g/mol

Functional groups

1,3,4-Oxadiazole, 4-chlorophenyl, and 4-methylphenyl groups

Application

Used in the pharmaceutical industry as a building block for the synthesis of various bioactive molecules, such as pharmaceuticals and agrochemicals.

Versatility

Its structure and properties make it a versatile intermediate for the development of new drugs and agrochemicals with potential therapeutic and agricultural applications.

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 3619-22-5 p-toluic hydrazide 
• 51771-25-6 4-Methyl-benzoic acid [1-(4-chloro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 23289-10-3 2-(4-chlorophenyl)-1,3,4-oxadiazole 
• 624-31-7 4-tolyl iodide 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 14062-78-3 N,N-dimethyl-4-toluamide 
• 827-58-7 2-p-tolyl-1,3,4-oxadiazole 
• 77420-62-3 N'-(4-methylbenzylidene)-4-chlorobenzohydrazide 
• 25563-06-8 N-methoxy-4-methylbenzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 59098-56-5 2-(4-chloro-phenyl)-5-{4-[2-(2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-[1,3,4]oxadiazole 
• 65205-22-3 2-(4-chloro-phenyl)-5-{4-[4-(4,5-diphenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 65205-18-7 2-(4-chloro-phenyl)-5-{4-[4-(4-chloro-5-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 65205-05-2 2-(4-chloro-phenyl)-5-{4-[4-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 65205-01-8 2-(4-chloro-phenyl)-5-{4-[4-(5-chloro-2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 59098-62-3 2-(4-chloro-phenyl)-5-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-[1,3,4]oxadiazole 
• 37430-95-8 2-(4-{4-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-trans-styryl}-phenyl)-2H-naphtho[1,2-d][1,2,3]triazole 
• 59151-72-3 2-(4-chloro-phenyl)-5-{4-[4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 
• 59151-80-3 2-(4-chloro-phenyl)-5-{4-[4-(4-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-[1,3,4]oxadiazole 

Relevant academic research and scientific papers

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles

Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 1, 3, 4-oxadiazoles.

A pharmaceutical intermediate the body is wicked oxadiazole compound synthesis method (by machine translation)

The present invention provides a following formula (I) of the oxadiazole compound shows wickedly synthetic method, said method comprising: in the organic solvent, the catalyst organic copper compound, in the presence of alkali and activator, a compound of formula (II) compound of formula (III) in the reaction in an inert atmosphere, thus formula (I) compounds, wherein R1 And R2 Are each independently H, C1 - C6 Alkyl, C1 - C6 Alkoxy, halogen or nitro; X is halogen. The method through the catalyst, alkali, organic solvent activator and the appropriate selection/combined, but to a high yield of the objective product, in the medical intermediate synthesis field and has a wide application and great industrial. (by machine translation)

Ligand-free Cu(ii)-mediated aerobic oxidations of aldehyde hydrazones leading to N,N′-diacylhydrazines and 1,3,4-oxadiazoles

A Cu(ii)-mediated synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles from aldehyde hydrazones has been developed. This is the first time that the synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles using N,N-dimethylamides as the acylation reagent and O2 in air as the oxidation reagent is reported. These reactions offered several advantages including simple workups, ligand-free inexpensive metal salts as mediators, high yields, and wide scope of substrates.

Ligand-free copper(0) catalyzed direct C-H arylation of 1,2,4-triazoles and 1,3,4-oxadiazoles with aryl iodides in PEG-400

A ligand-free copper catalyzed approach has been developed to the synthesis of 3,4,5-triaryl-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles by the direct arylation of corresponding 3,4-diaryl-1,2,4-triazoles and 2-aryl-1,3,4-oxadiazoles with aryl iodides using PEG-400 as reaction medium. The procedure is experimentally simple and free from addition of external chelating ligands or co-catalysts.

C-H arylation of azaheterocycles: A direct ligand-free and Cu-catalyzed approach using diaryliodonium salts

An efficient and high yielding Cu-catalyzed direct C-H arylation of azaheterocycles including oxadiazoles, thiadiazoles, benzoxazoles and benzothiazoles has been achieved by employing easily accessible diaryliodonium salts. the Partner Organisations 2014.

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.

Palladium-catalyzed deamidative arylation of azoles with arylamides through a tandem decarbonylation-C-H functionalization

A highly chemo-, regio-selective, and efficient palladium-catalyzed deamidative arylation of azoles with arylamides, as an aryl metal equivalent, has been developed. The reaction proceeds smoothly to generate the corresponding products in good yields via a tandem decarbonylation-C-H activation.

N-chlorosuccinimide/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles

A mixture of N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0]undec-7-ene oxidatively cyclizes structurally diverse acyl hydrazone, thereby providing an efficient and convenient method for the synthesis of various 2,5-disubstituted 1,3,4-oxadiazoles. The salient features of this method are mild reaction conditions, short reaction time, excellent yields, and simple workup procedure. Copyright

Trichloroisocyanuric acid-mediated one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles at ambient temperature

An efficient method for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles has been developed using trichloroisocyanuric acid (TCCA) at ambient temperature. A wide variety of aromatic as well as heterocyclic aldehydes exhibit condensation with a variety of acylhydrazines followed by oxidative cyclization to yield corresponding unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. Copyright Taylor & Francis Group, LLC.