10403-54-0

Upstream product

• 26087-01-4 (Z)-2-azido-1,3-diphenylprop-2-en-1-one 
• 873-67-6 benzonitrile oxide 
• 93-58-3 benzoic acid methyl ester 
• 120-46-7 1,3-diphenylpropanedione 
• 98-86-2 acetophenone 
• 2039-49-8 3,5-diphehylisoxazole 
• 98815-39-5 (Z)-3-amino-1,3-diphenylprop-2-en-1-one 
• 536-74-3 phenylacetylene 

Downstream Products

• 2039-49-8 3,5-diphehylisoxazole 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 119097-58-4 4-benzamido-3,5-dipenylisoxazole 
• 84655-38-9 (3,6-Diphenyl-4H-[1,2,4]oxadiazin-5-yl)-phenyl-methanone 
• 29329-38-2 5-phenyl-3-(p-tolyl)isoxazole 
• 26218-73-5 3,4-bis(4-methylphenyl)-1,2,5-oxadiazole-N-oxide 
• 84768-37-6 5-benzoyl-6-phenyl-3-p-tolyl-4H-1,2,4-oxadiazine 
• 16112-20-2 3,5-di(4′-methylphenyl)isoxazole 
• 26218-72-4 3,4-bis-(4-chloro-phenyl)-furazan 2-oxide 
• 84655-40-3 [3-(4-Chloro-phenyl)-6-phenyl-4H-[1,2,4]oxadiazin-5-yl]-phenyl-methanone 
• 98815-39-5 (Z)-3-amino-1,3-diphenylprop-2-en-1-one 
• 97015-57-1 2-benzamido-1,3-diphenyl-1,3-propanedione 
• 345652-72-4 N-(1-Benzoyl-2-oxo-2-phenyl-ethyl)-benzamidine 
• 119097-55-1 N-(1-Benzoyl-2-oxo-2-phenyl-ethyl)-N-methyl-benzamide 

Relevant academic research and scientific papers

KI/TBHP-mediated oxidative cross-coupling of enamines and carboxylic acids under metal-free conditions: A facile access to functionalized 2H-azirines

KI/TBHP-mediated oxidative cross coupling of enamines with carboxylic acids has been realized for the synthesis of functionalized 2H-azirines through the azirination of enamine intermediates. The metal-free strategy has several notable features, including the formation of C-O and C-N bonds in a one-pot procedure, broad functional group tolerance, good reaction yields, short reaction time, and high atom economy. It is the first example for direct formation of functionalized 2H-azirines via KI/TBHP-mediated intermolecular cross-coupling of enamines and carboxylic acids.

A simple green procedure for the synthesis of 2H-azirines

An efficient and environmentally friendly method preparing 2H-azirines in good yield has been achieved by microwave irradiation of vinyl azides in solvent free conditions.

Vinylnitrene formation from 3,5-diphenyl-isoxazole and 3-benzoyl-2-phenylazirine

Photolysis of 1 in argon-saturated acetonitrile yields 2, whereas in oxygen-saturated acetonitrile small amounts of benzoic acid and benzamide are formed in addition to 2. Similarly, photolysis of 2 in argon-saturated acetonitrile results in 1 and a trace amount of 3, whereas in oxygen-saturated acetonitrile the major product is 1 in addition to the formation of small amounts of benzoic acid and benzamide. Laser flash photolysis of 1 results in an absorption due to triplet vinylnitrene 4 (broad absorption with λmax at 360 nm, τ = 1.8 μs, acetonitrile) that is formed with a rate constant of 1.2 × 107 s-1 and decays with a rate constant of 5.6 × 105 s-1. Laser flash photolysis of 2 in argon-saturated acetonitrile likewise results in the formation of triplet vinylnitrene 4 but also ylide 5 (λmax at 440 nm, τ = 13 μs). The rate constant for forming 4 in argon-saturated acetonitrile is 1.6 × 107 s-1. In oxygen-saturated acetonitrile, vinylnitrene 4 reacts to form the peroxide radical 6 (λmax 360 nm, ～0.7 μs, acetonitrile) at a rate of 2 × 109 M-1s-1. Density functional theory calculations were performed to aid in the characterization of vinylnitrene 4 and peroxide 6 and to support the proposed mechanism for the formation of these intermediates.

A Copper-Catalyzed Synthesis of Pyrroles through Photochemically Generated Acylazirines

A synthesis of highly substituted 2,4-diacylpyrroles through a Cu-catalyzed dimerization of acylazirines generated in situ by a photochemical valence isomerization is described. The shown methodology allows the use of simple precursors and a readily avail

A photochemical one-pot three-component synthesis of tetrasubstituted imidazoles

Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, α-aminonitriles, and isoxazoles. Condensation of the first two components produces α-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C2-C3 bond of the acylazirine. The reaction mechanism was studied by DFT calculations. (Chemical Equation Presented)

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes 9a-9c were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole derived oxetanes show type T photochromism.

Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines

5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.

Metal-carbonyl-Induced Reaction of Isoxazoles. Ring Cleavage and Reduction by Hexacarbonylmolybdenum, Pentacarbonyliron, or Nonacarbonyldi-iron

In the presence of and water the isoxazoles (1a-f) undergo thermally induced reductive cleavage of the N-O bond to give β-amino enones in good yield.Similar results were obtained by the use of and water with photoirradiation, or of and water with heating.A mechanism involving an N-complexed isoxazolepentacarbonylmolybdenum or isoxazoletetracarbonyliron, and a - or -complexed (β-oxo vinyl)nitrene intermediate is proposed for the reactions.The complexed nitrene moiety could be reduced by the central metal in the presence of water to give amine.Furthermore, treatment of 2-benzoyl- 3-phenyl-2-H-azirine (8a), which is an isomer of 3,5-diphenylisoxazole, with the metal carbonyls and water also resulted in the formation of a β-amino enone possibly via the corresponding complexed (β-oxo vinyl)nitrene.An N-complexed isoxazole-pentacarbonylmolybdenum intermediate was prepared by the photoreaction of with 3,5-dimethylisoxazole.Its characterization, and chemical transformations, have been carried out to investigate the proposed mechanism.