25283-95-8

Upstream product

• 192332-48-2 N'-hydroxy-4-nitrobenzimidamide 
• 98-88-4 benzoyl chloride 
• 68451-75-2 C₁₄H₁₁N₃O₄ 
• 98-07-7 Benzotrichlorid 
• 192332-48-2 (Z)-4-nitrobenzamidoxime 
• 73289-49-3 N-acetyl methyl benzimidate 
• 1613-86-1 p-nitrophenylamidoxime 
• 37463-45-9 3-(4-nitrophenyl)-5-phenyl-4,5-dihydro-1,2,4-oxadiazole 
• 613-90-1 benzoyl cyanide 
• 100-46-9 benzylamine 
• 1011-84-3 4-nitrobenzohydroximoyl chloride 
• 188118-35-6 3-(4-Nitro-phenyl)-5-phenyl-[1,2,4]oxadiazole 4-oxide 
• 65696-81-3 3-anilino-3-phenyl-acrylonitrile 
• 109-92-2 ethyl vinyl ether 

Downstream Products

• 957470-97-2 [4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl](prop-2-yn-1-yl)amine 
• 54494-08-5 4-aminophenyl-5-phenyl-1,2,4-oxadiazole 

Relevant academic research and scientific papers

An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage

A high-yielding method for the synthesis of 2 H -1,3,5-oxadiazines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO

Abstract: A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system NaOH/DMSO at room temperature. The scope of the proposed procedure has been demonstrated by 15 syntheses from various amidoximes and aromatic aldehydes with 27–76% yields. The procedure is inapplicable to aliphatic aldehydes.

Oxidative cyclization of amidoximes and thiohydroximic acids: A facile and efficient strategy for accessing 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles

A facile and practical protocol has been developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles through oxidative cyclization of amidoximes and thiohydroximic acids, respectively at room temperature. Use of mild reaction

Microwave assisted synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from substituted amidoximes and benzoyl cyanides

We report herein the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from amidoximes and substituted or unsubstituted benzoyl cyanides under microwave irradiation. Substituted or unsubstituted O-carboxyphenyl amidoxime is a key intermediate of this alternative method developed for the synthesis of these heterocycles. These reactions employ simple synthetic protocols devoid of lengthy purification procedures and proceed with good yield.

1,2,4-Oxadiazole 4-oxides as nitrones in 1,3-dipolar cycloaddition reactions to vinyl ethers

1,2,4-Oxadiazole 4-oxides display nitronic reactivity and selectivities identical to those of N-methyl-C-phenyl nitrone, which is a typical acyclic nitrone, affording comparable amounts of endo- and exo-5-alkoxyisoxazolidines. The exo stereoisomers undergo an easy rearrangement under the reaction conditions to yield oxadiazolinic esters. The structures of the adducts have been confirmed by X-ray structures and spectroscopic data. A donor p-methoxyphenyl at the nitronic carbon slows down the cycloaddition rate, while an acceptor p-nitrophenyl retards the rearrangement of the exo adduct. 1,2,4-Oxadiazole 4-oxides undergo 1,3-dipolar cycloaddition reactions with vinyl ethers to afford endo adducts and labile exo adducts that rearrange to oxadiazolinicesters. The structures of the isolated products were assigned on the basis of spectroscopic data and X-ray analyses. Copyright

Formation and cyclization of N′-(benzoyloxy)benzenecarboximidamides

The formation of N′-(benzoyloxy)benzenecarboximidamides and their subsequent cyclization to 3,5-disubstituted 1,2,4-oxadiazoles in different solvents were studied. A probable reaction mechanism was proposed on the basis of the obtained results.

Novel synthesis of 1,2,4-oxadiazoles by condensation of arylamidoximes with N-substituted iminoethers

A new efficient route to 3,5-disubstituted-1,2,4-oxadiazoles 4a-j has been performed via the one-step reaction between arylamidoximes 1a-e and N-substituted iminoethers 2a-c. The structures of compounds 4 have been elucidated by mass spectrometry, infrared and 1H, 13C NMR measurements.

Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides

The cycloaddition of nitrile oxides to amidoximes is a general method for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides with the same or different substituents. The yields are only moderate since an equivalent amount of the nitrile oxide is consumed by reaction with the amine released in the fragmentation of the primary cycloadducts and reforms the amidoxime. With excess nitrile oxides the 1,2,4-oxadiazole-4-oxides undergo a disproportionation reaction to yield nitroso carbonyl intermediates and 1,2,4-oxadiazoles.

SYNTHESIS OF 3,5-DIARYL-1,2,4-OXADIAZOLES FROM TRICHLOROMETHYLARENES AND ARENEAMIDOXIMES

The interaction of trichloromethylarenes ArCCl3 with areneamidoximes Ar'C(NH2)=NOH was studied.The reaction in the absence of a solvent