22815-99-2

Usage

Synthesis Reference(s)

Synthetic Communications, 24, p. 1575, 1994 DOI: 10.1080/00397919408010158

Upstream product

• 59105-34-9 3-acetyl-5-(4-nitro-phenyl)-3H-[1,2,3,4]oxathiadiazole 2-oxide 
• 22816-00-8 N'-acetyl-4'-nitrobenzohydrazide 
• 75-36-5 acetyl chloride 
• 16687-60-8 5-(4-nitrophenyl)-2H-tetrazole 
• 75-77-4 chloro-trimethyl-silane 
• 64-19-7 acetic acid 
• 1000865-32-6 3-acetyl-5-methyl-2-(4-nitrophenyl)-1,3,4-oxadiazoline 
• 16687-60-8 5-(4-nitrophenyl)-1H-1,2,3,4-tetrazole 
• 108-24-7 acetic anhydride 
• 127-19-5 N,N-dimethyl acetamide 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 79-24-3 Nitroethane 
• 25996-47-8 p-nitrobenzaldehyde acetylhydrazone 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 25877-49-0 2-(4'-aminophenyl)-5-methyl-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Harnessing Autoxidation of Aldehydes: In Situ Iodoarene Catalyzed Synthesis of Substituted 1,3,4-Oxadiazole, in the Presence of Molecular Oxygen

Isobutyraldehyde underwent auto-oxidation in the presence of molecular oxygen to generate an acyloxy radical under a "metal-free" environment. They were subsequently exploited in situ to afford hypervalent iodines with p-anisolyl iodide which generated substituted 1,3,4-oxadiazoles in moderate to excellent yields from N′-arylidene acetohydrazides. The reaction strategy tolerated diverse substitution on the hydrazide substrates. Control experiments and literature precedence supported the formation of an in situ iodosylarene complex that facilitates the formation of products.

Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles

A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds via polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.

Isoxazoline derivative and application thereof in agriculture

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An efficient and inexpensive approach to the synthesis of 2-substituted and 2,5-disubstituted 1,3,4-oxadiazoles from arylhydrazides and orthoesters is reported using catalytic NH4Cl. The conditions are mild, and thus, compatible with a variety of functional groups. The optimized reaction is performed using 30 mol % of NH4Cl in 100% EtOH and is generally complete within 1 h for non-aromatic orthoesters and 2-10 h for aromatic orthoesters. The reaction permits both electron-releasing and electron-withdrawing groups on the arylhydrazide substrate. Most products are formed in high yields and require only minimal purification. Compared with earlier reports, the current reactions proceed in shorter time and require less of the orthoester.

Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

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One-pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles based on the reaction of N,N-dimethyl amides with acid hydrazides

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Tetrazoles: LIII. Microwave-activated acylation of 5-substituted tetrazoles

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Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part III. [1,2] Transformation of N,O-acetals: 3-Acyl-1,3,4-oxadiazolines

(Chemical Equation Presented) Various aldehyde and ketone acylhydrazones are synthesized and, under acylating conditions, cyclized into 3-acyl-1,3,4-oxadiazolines. The scope and limitations of these cyclizations and the possible side reactions (e.g. formation of the open-chain N,O-acylhydrazinocarbinols) are dissected. For the first time, simple, convenient and efficient dehydrogenations of 3-acyl-1,3,4-oxadiazolines to oxadiazoles by treatment with potassium permanganate, or more conveniently, with ammonium cerium(IV) nitrate (CAN) are presented. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-oxadiazolines, as well as that of aldehyde diacylhydrazones (open-chain isomers of 2,5-disubstituted 3-acyl-1,3,4- oxadiazolines) regenerates the parent carbonyl compounds.