79965-74-5

Upstream product

• 75-05-8 acetonitrile 
• 762292-75-1 2,2-difluoro-2-(4-methoxyphenyl)ethanol 
• 112545-98-9 2,2-difluoro-2-(4-methoxyphenyl)acetic acid ethyl ester 
• 696-62-8 para-iodoanisole 
• 177750-10-6 N-(1-(4-methoxy)phenylethyl)acetamide 
• 2475-92-5 4-methoxyacetophenone oxime 
• 267877-40-7 2-acetyl-3-(4-methoxyphenyl)isoxazol-5(2H)-one 
• 631-61-8 ammonium acetate 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 58518-78-8 p-methoxyphenacyl acetate 

Downstream Products

• 870637-74-4 5-bromo-2-(bromomethyl)-4-(4-methoxyphenyl)oxazole 
• 79965-85-8 4-(4-Methoxy-phenyl)-2-methyl-5-nitro-oxazole 
• 870637-73-3 5-Bromo-4-(4-methoxy-phenyl)-2-methyl-oxazole 

Relevant academic research and scientific papers

Hypervalent iodane mediated reactions of: N -acetyl enamines for the synthesis of oxazoles and imidazoles

A hypervalent iodane reagent used for the intramolecular cyclization of N-acetyl enamines and intermolecular cyclocondensation of enamines and nitriles was investigated. The reaction was performed under mild conditions and gave oxazoles and imidazoles, respectively, in moderate to excellent yields. This transformation exhibits good reactivity, selectivity and functional group tolerance. The selectivity of the intra- or intermolecular reaction is dependent on the structure of N-acetyl enamines.

Lewis acid-mediated defluorinative [3+2] cycloaddition/aromatization cascade of 2,2-difluoroethanol systems with nitriles

The properties of C?F bonds, including high thermal and chemical stability, make derivatization of organic fluorine-containing compounds by the activation of the C?F bond and subsequent functionalization quite challenging. We herein report a Lewis acid-mediated defluorinative cycloaddition/aromatization cascade of 2,2-difluoroethanols with nitriles as a novel synthetic method for the preparation of 2,4,5-trisubstituted oxazoles. This reaction, which involves cleavage of two C?F bonds and the consecutive formation of C?O and C?N bonds in a one-pot fashion, features a broad substrate scope and moderate to high reaction yields. Mechanistic studies revealed that the reaction is initiated by the Lewis acid-mediated ring closure of the 2,2-difluoroethanol to produce the fluoroepoxide intermediate. (Figure presented.).

Copper-catalyzed direct synthesis of iodoenamides from ketoximes

Iodide in copper's pathway: A new, efficient, and practical copper-catalyzed synthesis of Z-iodoenamides from readily available ketoximes has been developed (see scheme). The reaction was believed to proceed through a single-electron-transfer pathway. The corresponding Z-iodoenamides have been applied to the synthesis of substituted oxazoles, dienes, β-phenoxyl enamides, eneynes, β-acylenamides, and pyrroles (DCE=1,2-dichloroethane). Copyright

High-temperature rearrangements of 2-acylisoxazol-5(2H)-ones and related oxazoles

2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540°C under flash vacuum pyrolysis conditions, but at higher temperatures the expected oxazoles are accompanied by increasing amounts of isomeric 2,5-disubstituted oxazoles, as well as anilides and decomposition products of the 2,4-disubstituted oxazole. The rearrangement mechanisms have been studied by the use of 13C labelled substrates and p-substituted 3-arylisoxazolones. The 2,5-disubstituted oxazoles are considered to arise from 1H-azirines, and the anilides from the nitrone ketene isomer of the acylisoxazolone.