20662-92-4

Upstream product

• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 2835-06-5 phenylglycin 
• 75-05-8 acetonitrile 
• 103-79-7 1-phenyl-acetone 
• 108-24-7 acetic anhydride 
• 144-55-8 sodium hydrogencarbonate 
• 2248-46-6 ethyl 2,2-difluoro-2-phenylacetate 
• 591-50-4 iodobenzene 
• 29548-91-2 1-phenyl-1,1-difluoropropan-2-one 
• 29548-92-3 1,1-difluoro-1-phenylpropan-2-ol 
• 1160169-35-6 1-(3-methyl-2-phenyl-2H-azirin-2-yl)ethanone 
• 2157-50-8 propiophenone oxime 
• 50874-15-2 1-phenylprop-2-ynyl-1-amine 
• 591-51-5 phenyllithium 

Downstream Products

• 76346-79-7 2-<(Trimethylsilyl)methyl>-4-methyl-5-phenyloxazole 
• 76346-92-4 2-(3-Butenyl)-4-methyl-5-phenyloxazole 
• 1575-95-7 N-acetylbenzamide 
• 89149-91-7 5-bromomethyl-4-phenyl-2-methyloxazole 
• 76346-80-0 (E)-2-(2-Phenylvinyl)-4-methyl-5-phenyloxazole 
• 76346-81-1 (Z)-2-(2-Phenylvinyl)-4-methyl-5-phenyloxazole 

Relevant academic research and scientific papers

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles

Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.

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.).

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ3-iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl- λ3-iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ3-iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.

Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

Base-Induced Transformation of 2-Acyl-3-alkyl-2H-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways

An experimental study of base-induced transformation reaction of 2-acyl-3-alkyl-2H-azirines to oxazoles indicated that a deprotonation-initiated mechanism is involved, in addition to nucleophilic addition to the imine functionality. Calculations suggested

Metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and oxygen atoms: Iodine(III)-mediated synthesis of highly substituted oxazoles

The metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and O-atoms for the regioselective assembly of 2,4-disubstituted and 2,4,5-trisubstituted oxazole compounds has been achieved by the use of PhIO with TfOH or Tf 2NH. The present reaction could be applied to a facile synthesis of an anti-inflammatory drug.

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

Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3

An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI 2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various func

Efficient synthesis of multi-substituted oxazoles under solvent-free microwave irradiation

A new and efficient method for the synthesis of multi-substituted oxazoles from various carbonyl compounds has been developed using sequential treatment of carbonyl compounds with HDNIB and amides such as acetamide or benzamide under solvent-free microwave irradiation conditions.